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Product Details of [ 92-81-9 ]

CAS No. :92-81-9 MDL No. :MFCD00022256
Formula : C13H11N Boiling Point : -
Linear Structure Formula :- InChI Key :HJCUTNIGJHJGCF-UHFFFAOYSA-N
M.W : 181.23 Pubchem ID :7106
Synonyms :

Safety of [ 92-81-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 92-81-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 92-81-9 ]

[ 92-81-9 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 260-94-6 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
100% With carbon monoxide; hydrogen In tetrahydrofuran at 200℃; for 2h; other reagents, catalysts, temperature;
99% With C26H29ClIrNO3; hydrogen In 2,2,2-trifluoroethanol at 20℃; for 3h;
99% With benzo-15-crown-5; natrium; isopropanol In tetrahydrofuran at 0℃; for 0.0833333h; chemoselective reaction;
99% With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide In tetrahydrofuran Electrochemical reaction;
99% With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In isopropanol; acetonitrile at 100℃; for 48h; Autoclave; Glovebox; chemoselective reaction;
98% With boron trifluoride diethyl ether complex; sodium cyanotrihydridoborate In tetrahydrofuran for 8h; Heating;
98% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; potassium iodide at 40℃; for 12h;
98% With hantzsch ester; Orthoboric acid In 1,2-dichloro-ethane at 60℃; for 7h; chemoselective reaction;
96% With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex; C45H44IrN2P2 In dichloromethane-d2 at 20℃; Inert atmosphere;
96% With 1,3-dimethyl-2-imidazolidinone; natrium; <i>tert</i>-butyl alcohol In tetrahydrofuran; paraffin oil at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Procedure A) Substrate → SD → t-BuOH (non-polar substrate). General procedure: In a dry Schlenk tube (φ24) equipped with a glass-coated stirring bar (φ6 × 19 mm) undernitrogen, to a solution of substrate (0.50 mmol, 1.0 equiv) in a mixture of anhydrous DMIor HMPA (1.30-2.60 mL) and THF or DME (0.50-0.90 mL) was added sodiumdispersion (SD; ca 26 wt%, 230-800 mol%) dropwise (one drop of SD was added atintervals of 10 seconds) at 0 °C. Next, t-BuOH (2.3-8.0 equiv) was added dropwise (onedrop of t-BuOH was added at intervals of 5 seconds) at the same temperature.
96% With 1,3-dimethyl-2-imidazolidinone; natrium; <i>tert</i>-butyl alcohol In tetrahydrofuran; paraffin oil at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Procedure A) Substrate → SD → t-BuOH (non-polar substrate). General procedure: In a dry Schlenk tube (φ24) equipped with a glass-coated stirring bar (φ6 × 19 mm) undernitrogen, to a solution of substrate (0.50 mmol, 1.0 equiv) in a mixture of anhydrous DMIor HMPA (1.30-2.60 mL) and THF or DME (0.50-0.90 mL) was added sodiumdispersion (SD; ca 26 wt%, 230-800 mol%) dropwise (one drop of SD was added atintervals of 10 seconds) at 0 °C. Next, t-BuOH (2.3-8.0 equiv) was added dropwise (onedrop of t-BuOH was added at intervals of 5 seconds) at the same temperature.
95% With methanol; C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Sealed tube; Inert atmosphere;
95% With red phosphorus; lithium hydroxide monohydrate; potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere; regioselective reaction;
94% Stage #1: acridine With formic acid; triethylamine In N,N-dimethyl-formamide at 130℃; for 3h; Stage #2: With lithium hydroxide monohydrate; sodium hydroxide In ethanol at 100℃; for 1.5h; chemoselective reaction;
93% With phenylsilane In toluene at 20℃; for 12h;
92% Stage #1: acridine With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran Inert atmosphere; regioselective reaction;
92% With C13H8BrMnN2O5; potassium-t-butoxide In isopropanol at 80℃; for 24h; Sealed tube;
92.5% With iron(II) trifluoromethanesulfonate; hantzsch ester In chloroform-d1 at 40℃; for 21h; Inert atmosphere; Schlenk technique;
91% With hydrogen In lithium hydroxide monohydrate; isopropanol Heating; High pressure; chemoselective reaction;
90% With hydrogen In lithium hydroxide monohydrate at 20℃; for 24h; regioselective reaction;
90% With lithium; glacial acetic acid; Ethane-1,2-diamine In tetrahydrofuran at 0℃; for 5h; Reduction of acridine to 9,10-dihydroacridine: The following procedure was performed for the reduction of acridine to 9,10-dihydroacridine: A single-neck, 100-mL round-bottom flask was equipped with a magnetic stir bar and a septum equipped with a needle connected to a bubbler as a gas outlet. Acridine (1.00 g, 5.58 mmol), THF (19 mL), ethylenediamine (2.23 mL, 33.5 mmol, 6.0 equivalents), and acetic acid (0.479 mL, 8.37 mmol, 1.5 equivalents) were added to the flask, and the resulting solution was stirred while cooling to 0° C. Lithium (120 mg, 17 mmol, 3.0 equivalents) was added to the solution. The reaction mixture was allowed to slowly warm to 25° C. until TLC analysis showed the reaction to be complete (5 h). Saturated aqueous NH4Cl (40 mL) was added to reaction mixture, and the resulting mixture was stirred until the remaining lithium was quenched. The resulting mixture was concentrated under reduced pressure with a rotary evaporator until most THF was removed. The resulting mixture was poured to a 125-mL separatory funnel, and the product was extracted with Et2O (30 mL×3). The organic extracts were combined, dried over Na2SO4, filtered through cotton, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography ( SiO2, 2.5 to 10% EtOAc in hexanes) to give 9,10-dihydroacridine (905 mg, 90% yield) as a white solid. Data for 9,10-dihydroacridine: 1H NMR (300 MHz, CDCl3, 294K) δ 7.08 (m, 4H), 6.85 (td, 2H, J=7.4, 1.1 Hz), 6.66 (br d, 2H, J=7.4 Hz), 5.94 (s, 1H), 4.05 (s, 2H).).
88% With hydrogen In methanol at 120℃; for 4h; Autoclave; chemoselective reaction;
87% With 1,5-dimethylcyclohexa-1,4-diene; tris(pentafluorophenyl)borate In toluene at 125℃; for 18h; Glovebox; Sealed tube; Inert atmosphere;
87% With phenylsilane; trifluoromethane sulfonic acid silver salt In lithium hydroxide monohydrate Schlenk technique; Sealed tube; Green chemistry;
86% With hydrogen In toluene at 120℃; for 48h; Autoclave;
86% With C23H21MnN2O3P(1+)*Br(1-); potassium-t-butoxide; hydrogen In tetrahydrofuran at 120℃; for 16h; Autoclave; 4 Example 4 General procedure: In a glove box filled with argon, potassium tert-butoxide (5.6 mg, 0.05 mmol), and a manganese catalyst (0.005 mmol) were sequentially added to a 4 mL glass bottle with a stirrer, the manganese catalysts being Formula I to Formula IV, respectively. The manganese catalysts of the structure shown are recorded as manganese catalysts [Mn] -1, [Mn] -2, [Mn] -3, [Mn] -4), tetrahydrofuran (0.5 mL) and quinoline (0.25 mmol), Cap the bottle cap, insert a needle with a vent hole (length 3cm, hole diameter 1mm) into the bottle cap, put the glass bottle into the autoclave, and then remove the autoclave from the glove box. Replace the argon gas in the autoclave with hydrogen (3 × 10bar), then fill with 80bar hydrogen, and react at 120 ° C for 16h. After the reaction, the ice-water bath is cooled, and the gas in the autoclave is carefully released. The resulting reaction product system is sampled for The target product was obtained by GC quantification and separation by column chromatography. According to the method of Example 2, the manganese catalyst [Mn] -4 was used for catalytic hydrogenation of other types of nitrogen-containing unsaturated heterocyclic compounds. The structural formula and yield of each target product are listed in Table 3.
82% With formic acid; C29H32ClIrNO; anhydrous sodium formate In lithium hydroxide monohydrate for 16h;
80% With sodium hydroxide; 9-phenyl-10-benzyldecahydroacridine In propyl alcohol for 2h; Heating; other subst. acridines; in neutral media;
80% With sodium hydroxide; 9-phenyl-10-benzyldecahydroacridine In propyl alcohol for 2h; Heating;
80% With C18H2BF13; hydrogen In toluene at 25℃; for 2h;
80% With Co(BF4)2·6H2O; tris(2-diphenylphosphinophenyl)phosphine; hydrogen In tetrahydrofuran at 60℃; for 15h; Autoclave; chemoselective reaction;
80% With palladium 10% on activated carbon; ammsnium formate In ethanol at 80℃; for 12h; Schlenk technique; 3. EXPERIMENTAL SECTION General procedure: The typical procedure for Pd/C catalyzed decarboxylation-transfer hydrogenation (DTH) of quinoline carboxylicacids and transfer hydrogenation (TH) of quinolines: A mixtureof quinoline 1 or 3 (0.50 mmol), Pd/C (10.0 mg, 10 wt%palladium on activated carbon paste and 50% moisture, 0.9mol% [Pd] based on starting material 1 or 3) in ethanol (3mL) was added into a Schlenk flask (25 mL) at room temperature.Then ammonium formate (126 mg, 2.0 mmol, 4.0equiv) was added and the mixture was stirred at 80 °C. Thereaction was monitored by thin layer chromatography (TLC).After the reaction was finished, the solvent was evaporatedunder reduced pressure and the residue was purified by columnchromatography (petroleum ether/ethyl acetate 20:1 to5:1) to provide 1,2,3,4-tetrahydroquinolines 2
79% With 1,5-dimethoxy-1,4-cyclohexadiene; C40H55PRhS(1+)*C32H12BF24(1-) In benzene at 20℃; for 18h; Glovebox; Sealed tube;
78% With tetrahydroxydiborane; copper (II) acetate In acetonitrile at 80℃; for 12h; Schlenk technique; chemoselective reaction; 4.1.1. Typical procedure for the synthesis of 1,2,3,4-tetrahydroquinoline (2a) General procedure: A 20 mL Schlenk tube was charged with quinoline (1a; 65 mg,0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4 (135 mg,1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 40 °C for 8 h until the reaction was completed (TLC), then cooled to room temperature and concentrated under reduced pressure. Water (10 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography with petroleum ether/ethyl acetate (8:1) as an eluent to give a brown liquid (2a: 65 mg, 98% yield).
77% With hydrogen In various solvent(s) at 170℃; for 7h; also Re/Al2O3 was tested;
76% With borane-ammonia; tris(pentafluorophenyl)borate In toluene at 80℃; for 8h; Schlenk technique; Inert atmosphere;
75% With dibenzo-18-crown-6; lithium In propyl alcohol; n-Pentane at 0℃; for 0.0833333h; Inert atmosphere; 5 Example 5 10ml single neck flask, a nitrogen atmosphere, was added 20.8 mg (3.0 mmol) lithium reagent (lithium sand, particle size <100μm), dibenzo-18-crown -6 772.3μl (3.0mmol), 1ml n-pentane, 0 stirring 5min. A substrate solution is prepared. A 1.5 ml centrifuge tube was taken, and 89.6 mg (0.5 mmol) of acridine, 224.2 μl (3.0 mmol) of n-propanol, 1 ml of n-pentane were added, shaken, taken into a syringe, and washed with 1 ml of n-pentane, and taken into a syringe. Add the prepared mixed solution to a single-mouth bottle and stir at 0 ° C for 5 min. The reaction was quenched with 2ml of saturated aqueous NaHCO3, warmed to room temperature. Diethyl ether was added and extracted with saturated aqueous sodium chloride solution, the organic phase was dried, concentrated, and column chromatographed to give 68.0mg of the title compound in 75% yield.
73% With palladium diacetate; Cs2CO3; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane In lithium hydroxide monohydrate at 20℃; for 10h; Schlenk technique; Inert atmosphere;
72% With ammsnium formate In methanol for 0.15h; Heating;
70% With lithium; nickel (II) chloride In tetrahydrofuran at 20℃;
70% With hydrogen
70% With hydrogen In ethanol for 48h; 3 EXAMPLE 3; Preparation of 2,4-Diamino-6-(9,10-dihydroacridin-9-yl)methylpteridine (Formula I: Ar=6-(2,4-diaminopteridine); X=N; W=CH2; Z=CH2; m=n=0);.Raney Ni (1 g) was added to a solution of acridine (1 g, 5.58 mmol) in EtOH (20 mL), and the mixture was shaken under a hydrogen atmosphere (50 psi) for 2 days. Additional EtOH (200 mL) was added, and the Ni catalyst was removed by filtration. Evaporation of filtrate and recrystallization of the residue from MeOH afforded colorless needles of 5,10-dihydroacridine (0.7 g, 70% yield); mp 169-170° C. A portion of this material (0.224 g, 1.18 mmol) was dissolved in dry THF (10 mL) under N2, and the solution was cooled to 0° C., and NaH (50% oil suspension containing 0.119 g, 4.7 mmol) was added in small portions with magnetic stirring After 10 min, 2,4-diamino-6-bromomethylpteridine hydrobromide (0.100 g, 0.392 mmol) was added slowly with continued stirring, and the reaction mixture was allowed to warm to room temperature and stirred overnight. Excess sodium hydride was destroyed with a small drops of AcOH, and the solvents were removed by rotary evaporation. Flash chromatography of the residue on silica gel with 9:1 ChCl3-MeOH as the eluent afforded the title compound, 2,4-diamino-6-(9,10-dihydroacridin-9-yl)methylpteridine, as a yellow-brown solid (ca. 10% yield); mp>250° C. dec. MS (FAB m/z (M+1)=370.1785.
67% With manganese(I) pentacarbonyl bromide; hydrogen In tetrahydrofuran at 130℃; for 8h;
51% With hydrogen In toluene at 20℃; for 48h; Glovebox; Autoclave;
47% Stage #1: acridine With glacial acetic acid In ethanol for 0.5h; Reflux; Stage #2: With sodium cyanotrihydridoborate In ethanol for 1.5h; Reflux; Stage #3: With ammonia In lithium hydroxide monohydrate 4.2.19. 9,10-Dihydroacridine (25) A mixture of acridine (24) (10.0 g, 55.8 mmol) and AcOH (6.01 g, 5.73 mL, 100 mmol) were added to absolute EtOH (100 mL) and heated at reflux for 30 min before the addition of NaCNBH3 (6.66 g, 106 mmol). The solution was heated at reflux for a further 1.5 h, cooled and the solvent removed by rotary evaporation. The white residue was basified with aqueous NH3 (200 mL) and extracted with Et2O (3×100 mL). The organic extract was evaporated and the white precipitate was recrystallised from 95% EtOH to yield 25 as cream coloured needles (4.76 g, 47%), mp 171-172 °C (lit.28 166-169 °C). 1H NMR (CDCl3, 500 MHz): δ 4.06 (s, 2H), 5.95 (br s, 1H), 6.67 (d, J=8.0 Hz, 2H), 6.86 (t, J=7.5 Hz, 2H), 7.06-7.11 (m, 4H). The 1H NMR spectral data coincided with those reported in the literature.29 LREI-MS: m/z (%): 180 (100) [M-H]+.
45.1% With nickel (II) chloride; BH3 In tetrahydrofuran; methanol for 1h; Ambient temperature;
43% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; N-methylamine hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; Irradiation;
32% With hydrogenchloride; isopropanol In lithium hydroxide monohydrate for 16h; Inert atmosphere; UV-irradiation;
30% With platinum; hydrogen In methanol at 40℃; Schlenk technique; Sealed tube;
26% With 2,6-bis((1H-pyrazol-1-yl)methyl)pyridine; borane-ammonia complex; NiCl2·6H2O In methanol at 25℃; for 0.5h; Inert atmosphere;
24 % Turnov. With potassium hydroxide; carbon monoxide; lithium hydroxide monohydrate In methanol at 150℃; for 1h;
With sodium mercury amalgam; ethanol
With hydrogenchloride; zinc powder
With sodium hydroxide; sodium dihydrosulfite; lithium hydroxide monohydrate Reagens 4:Alkohol;
With sodium mercury amalgam; ethanol bei der Reduktion;
With diethyl ether; ethanol; natrium
With 1,4-dioxane; nickel Hydrogenation.unter Normaldruck;
With 1,4-dioxane; nickel Hydrogenation;
With lithium aluminium hydride; diethyl ether; benzene
With potassium hydroxide; benzylic alcohol
With 1,4-dioxane; nickel Hydrogenation;
50 mg With carboxylate VIII In ethanol at 20℃; for 2h;
24 % Turnov. With potassium hydroxide; carbon monoxide; lithium hydroxide monohydrate In methanol at 150℃; for 1h;
50 % Turnov. With hydrogen In n-octane at 100℃; for 1h;
With C21H13BF8; hydrogen In (2)H8-toluene at 105℃; for 17h; Inert atmosphere; Cooling with liquid nitrogen;
With LiAlH4 In tetrahydrofuran S.1.1 Synthesis of 9,10-dihydroacridine of Reaction Scheme 1 Synthesis Example 1-1 Synthesis of 9,10-dihydroacridine of Reaction Scheme 1 Under a nitrogen atmosphere, acridine (17.19 g, 95.92 mmol) and THF (300 ml) were introduced into a round-bottom flask. At 0° C., LiAlH4 (14.56 g, 383.66 mmol) was slowly added in halves twice thereto, followed by stirring at room temperature for 4 hours. At 0° C., the resultant product was slowly added with a sodium bicarbonate solution, and then extracted with methylene chloride and distilled water. The extracted layer was dried with sodium sulfate so as to filtrate and concentrate an organic solvent. Then, the resultant product was columned by methylene chloride and hexane (n-Hexane:MC=8:2) so as to obtain a required compound, 9,10-dihydroacridine (white solid, 14 g, 82%). 1H NMR: 3.8 (s, 2H), 4.0 (s, 1H), 6.3 (t, 2H), 6.5 (dd, 2H), 6.8 (m, 4H).
100 %Chromat. With hydrogen In toluene at 60℃; for 2.5h; Autoclave; chemoselective reaction;
Multi-step reaction with 2 steps 1: 1-(4,4,5,5-tetramethyl-1,3,2-dioxaboronia-2-yl)-1,4-diazabicyclo[2.2.2]octane tetrakis-(pentafluorophenyl)borate / 1 h / 20 °C / Inert atmosphere 2: lithium hydroxide monohydrate / dichloromethane
> 95 %Spectr. Stage #1: acridine With phenylsilane; lithium triethylhydroborate In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With lithium hydroxide monohydrate In methanol at 20℃; for 2h;
72 %Spectr. With [Cp(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Ru(pyridine)2][PF6]; potassium-t-butoxide; isopropanol at 70℃; for 8h; Glovebox; Schlenk technique; Inert atmosphere;
84 %Spectr. With CH2F3O3S(1-)*C9H21Sn(1+); hydrogen In 1,2-dichloro-benzene at 120℃; for 32h; Inert atmosphere;
With triisopropyltin triflate[18b]; hydrogen In 1,2-dichloro-benzene at 120℃; for 32h; 14 Hydrogenation of acridine A solution of acridine (35.8 mg, 0.2 mmol) in 1 ,2-dichlorobenzene (0.7 mL) was added to /Pr3SnOTf (7.9 mg, 0.02 mmol) in a Wilmad high pressure NMR tube fitted with a PV-ANV PTFE valve. H2 was admitted up to a pressure of 10 bar (at RT). The reaction mixture was heated in an oil bath to 120 °C for 32 h. 1 H NMR spectroscopic analysis indicated 84 % conversion to acridane (final NMR spectrum recorded at 70 °C to ensure homogeneity). Hydrogenation of n-butyl acrylate
Multi-step reaction with 2 steps 1.1: 1-(4,4,5,5-tetramethyl-1,3,2-dioxaboronia-2-yl)-1,4-diazabicyclo[2.2.2]-octane tris(pentafluorophenyl)hydridoborate / toluene / 3 h / Inert atmosphere 1.2: 3 h / 20 °C / Glovebox; Inert atmosphere 2.1: lithium hydroxide monohydrate / hexane
With [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)]; hydrogen In neat (no solvent) at 75℃; for 18h;
> 42 %Spectr. With hydrogen; ((+)-1,2-bis[(2R,5R)-2,5-diisopropylphospholano]benzene)Co(CO)2H In hexadeuterobenzene at 100℃; for 18h; Darkness;
With ammonia borane; copper(II) sulphate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction;
99 %Chromat. With hydrogen In isopropanol at 80℃; for 13h; Autoclave;
Reduction of acridine to 9,10-dihydroacridine:
The following procedure was performed for the reduction of acridine to 9,10-dihydroacridine:
90 %Spectr. With formic acid; C19H24ClIrN4O2; lithium hydroxide monohydrate; anhydrous sodium formate at 45℃; for 6h; Schlenk technique; Inert atmosphere;

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  • 2
  • [ 75-44-5 ]
  • [ 92-81-9 ]
  • [ 857571-05-2 ]
YieldReaction ConditionsOperation in experiment
With pyridine; toluene
  • 3
  • [ 92-81-9 ]
  • [ 74-88-4 ]
  • [ 4217-54-3 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
75% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -5 - 20℃; Schlenk technique; Inert atmosphere;
With ethyllithium
Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0 - 20℃; Schlenk technique; Inert atmosphere;

  • 4
  • [ 92-81-9 ]
  • [ 260-94-6 ]
YieldReaction ConditionsOperation in experiment
99% With diethylazodicarboxylate In chloroform; toluene at 20℃; for 12h; General procedure of the DEAD-mediated dehydrogenationof 1,2,3,4-tetrahydroquinolines General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1,2,3,4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wt% in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl3 (1.0 mL) was added. The reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with EtOAc:hexane (1:5) to give quinolines. In case of 2f and 2m, the product spot was close to the spot of the remained DEAD. To eliminate the remained DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred.[19] After 10 min, the reaction mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with CHCl3:hexane (1:1) to give quinolines.
99% With trimethylamine-N-oxide; Co(salophen)-HQ In dimethyl sulfoxide at 90℃; for 36h; Schlenk technique; Green chemistry;
99% With air; nitrogen/phosphorus co-doped porous carbon In lithium hydroxide monohydrate at 100℃; for 12h; Green chemistry;
98% With 4-tert-Butylcatechol In chloroform; lithium hydroxide monohydrate at 20℃; for 8h;
97% With carbon dioxide; 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine; Bromoeosine In dimethyl sulfoxide at 25 - 30℃; for 48h; Irradiation;
96% Stage #1: acridine With 2',3',4',5'-tetra-O-acetylriboflavin; oxygen In acetonitrile for 0.0333333h; Green chemistry; Stage #2: In acetonitrile at 20℃; for 8h; Sealed tube; Irradiation; Green chemistry; 3.2. General Procedure for the Photocatalytic Oxidation Reaction. General procedure: A mixture of 9 (0.2 mmol) and 7 (0.01 mmol, 5.4 mg) was dissolved in acetonitrile(0.4 mL), and the solution was bubbled with O2 for 2 min. The flask was closed andstirred at room temperature under an O2 atmosphere (balloon) with irradiation by blueLEDs during the indicated reaction time (Figure 2). After that, H2O (2 mL) was added,and the reaction product was extracted with AcOEt (3 x 2 mL). The combined organicphases were dried over MgSO4, filtered and evaporated under reduced pressure (15 Torr)to get the crude product, which was purified by flash column chromatography on silicagel (n-hexane/AcOEt gradients). The adducts 10 and 12 were identified by comparison oftheir NMR data with those of the literature (Supplementary Materials, NMR spectra).
94% With air In N,N-dimethyl acetamide at 120℃;
90% With 4-tert-Butylcatechol; oxygen In lithium hydroxide monohydrate at 20℃; for 20h; Green chemistry; chemoselective reaction; The general procedure of oxidative dehydrogenation General procedure: N-heterocycle substrate (0.2 mmol), Na-AMO (20 mg, 10 mol%), catechol Q-2 (3.3 mg, 0.02 mmol) was added into a reaction tube. The reaction tube was filled and protected with oxygen using a O2 balloon, then H2O was added into the reaction tube with a syringe. The reaction was allowed to react at room temperature for 20 h. After completion of reaction, the resulting mixture was filtered, washed with EtOAc and extracted by EtOAc. The organic phases were combined, washed with brine and dried with Na2SO4. Next, organic solution was concentrated under reduced vacuum to give the crude product. Finally, the product was purified by silica gel chromatography to yield the pure product.
87% With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In n-heptane at 100℃; for 12h; Autoclave;
84% With perylene diimide covalent immobilized to SiO2 nanospheres; air In N,N-dimethyl acetamide at 20℃; UV-irradiation;
79% With hydrogenchloride; C13H25NO5S(1-)*Na(1+); oxygen; NaNO2 In lithium hydroxide monohydrate; acetonitrile at 35℃; for 12h;
79% With oxygen; iron(II) chloride In para-xylene; dimethyl sulfoxide at 110℃; for 20h; Schlenk technique; Typical Procedure General procedure: To a Schlenk tube equipped with a magnetic stir bar were added8-methyl-1,2,3,4-tetrohydroquinoline (0.50 mmol), FeCl2 (1.9mg, 1.5·10-2 mmol), DMSO (31.2 mg, 0.4 mmol), and p-xylene (1mL). The reaction mixture was stirred at 110 °C under anoxygen atmosphere using a balloon and monitored by TLC. Afterthe reaction, the mixture was cooled to room temperature andpurified using flash chromatography (hexane-EtOAc, 10:1) togive the corresponding product 8-methylquinoline in 70% yield.8-MethylquinolineColorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1 H), 8.10(m, 1 H), 7.64 (d, J = 4.0 Hz, 1 H), 7.54 (m, 1 H), 7.43-7.35 (m, 2H) 2.82 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 149.2, 147.3,137.1, 136.3, 129.6, 128.3, 126.3, 125.9, 120.8, 18.2. HRMS: m/zcalcd for [C10H9N + H+]: 144.0813; found: 144.0813.
74% With potassium-t-butoxide In o-dimethylbenzene at 140℃; for 36h; Inert atmosphere;
66% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; Co(dmgH)<SUB>2</SUB>(4-MeCO<SUB>2</SUB>Py)Cl In lithium hydroxide monohydrate at 28℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;
54% With manganese(III) triacetate; acetylacetone In glacial acetic acid for 0.0166667h; Heating;
With chromium(III) oxide; sulfuric acid
With sulfuric acid at 100℃;
With glacial acetic acid; NaNO2
With potassium dichromate||potassium bichromate||K2Cr2O7||Cr2O7K2; sulfuric acid
at 300℃;
With ferric(III) chloride In ethanol; lithium hydroxide monohydrate at 50℃; for 0.5h;
100 %Chromat. With platinum; oxygen In methanol at 40℃; Schlenk technique; Sealed tube;
With oxygen at 80℃; for 6h; Green chemistry; chemoselective reaction;
23.3 mg With dihydrogen peroxide at 45℃; for 6h;
With oxygen; C41H27F4IrN5(1+)*Cl(1-) In acetonitrile at 20℃; for 24h; Irradiation;

Reference: [1]Bang, Saet Byeol; Kim, Jinho [Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298]
[2]Manna, Srimanta; Kong, Wei-Jun; Bäckvall, Jan-E. [Chemistry - A European Journal, 2021, vol. 27, # 55, p. 13725 - 13729]
[3]Beller, Matthias; Lu, Guo-Ping; Ma, Rui; Neumann, Helfried; Shan, Hongbin; Sun, Kangkang; Wang, Peng [Chemical Science, 2022]
[4]Jawale, Dhanaji V.; Gravel, Edmond; Shah, Nimesh; Dauvois, Vincent; Li, Haiyan; Namboothiri, Irishi N.N.; Doris, Eric [Chemistry - A European Journal, 2015, vol. 21, # 19, p. 7039 - 7042]
[5]Riemer, Daniel; Schilling, Waldemar; Goetz, Anne; Zhang, Yu; Gehrke, Sascha; Tkach, Igor; Hollóczki, Oldamur; Das, Shoubhik [ACS Catalysis, 2018, vol. 8, # 12, p. 11679 - 11687]
[6]Chinchilla, Rafael; Torregrosa-Chinillach, Alejandro [Molecules, 2021, vol. 26, # 4]
[7]Wang, Ming; Fan, Qiaoling; Jiang, Xuefeng [Organic Letters, 2018, vol. 20, # 1, p. 216 - 219]
[8]Tang, Tao; Bi, Xiuru; Meng, Xu; Chen, Gexin; Gou, Mingxia; Liu, Xiang; Zhao, Peiqing [Tetrahedron Letters, 2020, vol. 61, # 5]
[9]Cui, Xinjiang; Li, Yuehui; Bachmann, Stephan; Scalone, Michelangelo; Surkus, Annette-Enrica; Junge, Kathrin; Topf, Christoph; Beller, Matthias [Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658]
[10]Su, Chenliang; Yu, Kunyi; Zhang, Hanjie; Zhu, Yongfa [European Journal of Organic Chemistry, 2020, vol. 2020, # 13, p. 1956 - 1960]
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[12]Zhou, Weiyou; Taboonpong, Piyada; Aboo, Ahmed Hamdoon; Zhang, Lingjuan; Jiang, Jun; Xiao, Jianliang [Synlett, 2016, vol. 27, # 12, p. 1806 - 1809]
[13]Liu, Tingting; Wu, Kaikai; Wang, Liandi; Yu, Zhengkun [Advanced Synthesis and Catalysis, 2019, vol. 361, # 17, p. 3958 - 3964]
[14]Sahoo, Manoj K.; Balaraman, Ekambaram [Green Chemistry, 2019, vol. 21, # 8, p. 2119 - 2128]
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[16]Graebe; Caro [Justus Liebigs Annalen der Chemie, 1871, vol. 158, p. 275]
[17]Boes [Chemisches Zentralblatt, 1915, p. II,711]
[18]Drosdow; Tschernzow [Zhurnal Obshchei Khimii, 1951, vol. 21, p. 1710,1713; engl. Ausg. S. 1885, 1887]
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[21]Location in patent: experimental part Desbois, Nicolas; Szollosi, Anna; Maisonial, Aurélie; Weber, Valérie; Moreau, Emmanuel; Teulade, Jean-Claude; Chavignon, Olivier; Blache, Yves; Chezal, Jean Michel [Tetrahedron Letters, 2009, vol. 50, # 49, p. 6894 - 6896]
[22]Ge, Danhua; Hu, Lei; Wang, Jiaqing; Li, Xingming; Qi, Fenqiang; Lu, Jianmei; Cao, Xueqin; Gu, Hongwei [ChemCatChem, 2013, vol. 5, # 8, p. 2183 - 2186]
[23]Bi, Xiuru; Tang, Tao; Meng, Xu; Gou, Mingxia; Liu, Xiang; Zhao, Peiqing [Catalysis science and technology, 2020, vol. 10, # 2, p. 360 - 371]
[24]Llopis, Natalia; Gisbert, Patricia; Baeza, Alejandro; Correa-Campillo, Jara [Advanced Synthesis and Catalysis, 2022, vol. 364, # 6, p. 1205 - 1210]
[25]Echevarría, Igor; Vaquero, Mónica; Manzano, Blanca R.; Jalón, Félix A.; Quesada, Roberto; Espino, Gustavo [Inorganic Chemistry, 2022, vol. 61, # 16, p. 6193 - 6208]
  • 5
  • [ 92-81-9 ]
  • 1,2,3,4,4a,5,6,7,8,9,9a,10-dodecahydro-acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-dioxane; nickel at 100℃; Hydrogenation;
  • 6
  • [ 92-81-9 ]
  • (+/-)-(4aSR,9aRS)-1,2,3,4,4a,9,9a,10-octahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-dioxane; copper oxide-chromium oxide at 190℃; Hydrogenation;
  • 7
  • [ 578-95-0 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
95% With phenylphosphane at 140℃; for 24h;
91% With borane-THF In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;
88% With borane-THF In tetrahydrofuran Reflux; Inert atmosphere;
80% With iodine; magnesium In methanol at 20℃; for 3h;
80% With sodium In butan-1-ol at 110℃;
75% Stage #1: 10H-acridin-9-one With borane-THF In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃;
72% With sodium In pentan-1-ol Heating;
With sodium amalgam; ethanol
With i-Amyl alcohol; sodium
With borane-THF In tetrahydrofuran for 4h; Inert atmosphere; Reflux; tert-Butyl Acridine-10(9H)-carboxylate General procedure: A two-necked 20-mL round-bottomed flask equipped with a magnetic stirring bar was charged with acridone 11 (195 mg, 1.00 mmol), and THF (2.5 mL). To the solution was added BH3*THF (1.08 M in THF, 1.3 mL, 1.4 mmol) at room temperature. The reaction mixture was heated at reflux for 4 h. The reaction was quenched with brine and 2 M aqueous NaOH, and the mixture was extracted with ether three times. The combined organic extracts were washed with saturated aqueous NaHCO3, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to afford the crude dihydroacridine 12 as a colorless solid, which was used to the next reaction without further purification. A 50-mL round-bottomed flask equipped with a magnetic stirring bar was charged with 12, Boc2O (766 mg, 3.51 mmol), and MeCN (3.3 mL). To the solution was added DMAP (203 mg, 1.66 mmol) at 0°C and stirring was continued for 11 h at room temperature. The reaction was diluted with ether. The mixture was washed with saturated aqueous NH4Cl and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to leave the residue, which was purified by silica gel column chromatography(hexanes-EtOAc= 9 : 1) to afford 13 (226 mg, 0.803 mmol, 80%).
With borane-THF In tetrahydrofuran for 4h; Reflux; General procedure: A two-necked 20-mL round-bottomed flask equipped witha magnetic stirring bar was charged with acridone (195 mg, 1.00 mmol), and THF (2.5 mL). To thesolution was added BH3THF (1.08 M in THF, 1.3 mL, 1.4 mmol) at room temperature. The reactionmixture was heated to reflux for 4 h, after which time TLC (hexanes-EtOAc = 3:1) indicated completeconsumption of acridone. The reaction was quenched with brine and 2 M aqueous NaOH, and the mixturewas extracted with Et2O three times. The combined organic extracts were washed with saturated aqueousNaHCO3, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated underreduced pressure to afford the crude dihydroacridine as a colorless solid, which was used for the nextreaction without further purification.
With borane-THF In tetrahydrofuran for 4h; Reflux; Inert atmosphere;
With borane-THF In tetrahydrofuran at 80℃; Inert atmosphere;
With borane-THF In tetrahydrofuran for 4h; Reflux; Inert atmosphere;

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[6]Location in patent: experimental part Desbois, Nicolas; Szollosi, Anna; Maisonial, Aurélie; Weber, Valérie; Moreau, Emmanuel; Teulade, Jean-Claude; Chavignon, Olivier; Blache, Yves; Chezal, Jean Michel [Tetrahedron Letters, 2009, vol. 50, # 49, p. 6894 - 6896]
[7]Charbit, Jean Jacques; Galy, Anne Marie; Galy, Jean Pierre; Barbe, Jacques [Journal of Chemical and Engineering Data, 1989, vol. 34, # 1, p. 136 - 137]
[8]Kliegl; Broesamle [Chemische Berichte, 1936, vol. 69, p. 197,201] Drosdow; Tschernzow [Zhurnal Obshchei Khimii, 1951, vol. 21, p. 1710,1713; engl. Ausg. S. 1885, 1887]
[9]Reed [Journal of the Chemical Society, 1944, p. 679]
[10]Cho, Hidetsura; Iwama, Yusuke; Okano, Kentaro; Tokuyama, Hidetoshi [Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 4, p. 354 - 363]
[11]Iwama, Yusuke; Noro, Takahiro; Okano, Kentaro; Cho, Hidetsura; Tokuyama, Hidetoshi [Heterocycles, 2014, vol. 8, # 2, p. 1433 - 1444]
[12]Jiang, Jian; Zhang, Wen-Man; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian [Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3622 - 3630]
[13]Li, Weiyu; Xu, Hao; Zhou, Lei [Organic and Biomolecular Chemistry, 2021, vol. 19, # 25, p. 5649 - 5657]
[14]Jiang, Huanfeng; Song, Qinghao; Sun, Yanping; Zhang, Min; Zhao, He [Chinese Journal of Chemistry, 2022, vol. 40, # 3, p. 371 - 377]
  • 8
  • [ 260-94-6 ]
  • [ 20178-49-8 ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
  • [ 1658-08-8 ]
  • 9
  • [ 260-94-6 ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
With Rh/Al2O3; hydrogen; In methanol; at 100℃; under 30003 - 33753.4 Torr; for 0.5h;Autoclave; General procedure: The acridine derivative 1, 3 or 5 (0.046 mmol) and Rh/Al2O3 (2 mg, 0.0008 mmol) in 0.4 mL of MeOH were put in a stainless steel autoclave. The solution was degased 3 times under hydrogen. The reaction mixture was then stirred at 40 bar H2 and heated at 100 C, for requested time (the final pressure was 45 bar). The reaction mixture was filtrated through celite, the solvent evaporated and the crude product analyzed by NMR without further purification
  • 10
  • [ 260-94-6 ]
  • [ 20178-49-8 ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
  • [ 1658-08-8 ]
  • [ 92039-20-8 ]
  • 11
  • [ 260-94-6 ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
  • [ 1658-08-8 ]
  • [ 92039-20-8 ]
  • 12
  • [ 260-94-6 ]
  • [ 92-81-9 ]
  • (+/-)-(4aSR,9aRS)-1,2,3,4,4a,9,9a,10-octahydroacridine [ No CAS ]
  • (+/-)-(4aRS,9aRS)-1,2,3,4,4a,9a,10-octahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With hydrogen In decalin at 150℃; for 0.166667h;
With hydrogen In decalin at 150℃; for 0.166667h;
  • 13
  • [ 13209-38-6 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
at 650℃;
  • 14
  • [ 92-81-9 ]
  • [ 4761-00-6 ]
  • [ 87742-37-8 ]
  • 15
  • [ 92-81-9 ]
  • [ 1658-08-8 ]
  • trans,syn,trans-perhydroacridine [ No CAS ]
  • (4aα,8aα,9aβ,10aα)-Tetradecahydroacridine [ No CAS ]
  • (4aα,8aα,9aα,10aβ)-Tetradecahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen In decalin at 250℃; Yield given. Yields of byproduct given;
  • 18
  • [ 6540-78-9 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
99% With phenylphosphane at 140℃; for 10h;
  • 20
  • [ 13213-90-6 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
95% at 650℃;
  • 21
  • [ 92-81-9 ]
  • [ 1026296-45-6 ]
  • 1-(9H-Acridine-10-carbonyl)-3-(2,6-diisopropyl-phenyl)-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In diethyl ether for 16h; Ambient temperature;
  • 22
  • [ 92-81-9 ]
  • [ 20178-49-8 ]
  • [ 260-94-6 ]
  • [ 3295-64-5 ]
  • [ 1658-08-8 ]
  • [ 92039-20-8 ]
  • 23
  • [ 92-81-9 ]
  • [ 1712-69-2 ]
  • [ 260-94-6 ]
  • [ 4132-48-3 ]
  • 24
  • [ 92-81-9 ]
  • [ 384-64-5 ]
  • [ 260-94-6 ]
  • [ 161361-16-6 ]
YieldReaction ConditionsOperation in experiment
In various solvent(s) at 250 - 290℃; ΔG(excit.), ΔH(excit.), ΔS(excit.);
  • 25
  • [ 3295-64-5 ]
  • palladium [ No CAS ]
  • hydrogen [ No CAS ]
  • [ 92-81-9 ]
  • 26
  • [ 3295-64-5 ]
  • selenium [ No CAS ]
  • [ 92-81-9 ]
  • 27
  • [ 3295-64-5 ]
  • palladium [ No CAS ]
  • hydrogen [ No CAS ]
  • [ 260-94-6 ]
  • [ 92-81-9 ]
  • 28
  • [ 5176-15-8 ]
  • [ 7732-18-5 ]
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • sodium amalgam [ No CAS ]
  • [ 260-94-6 ]
  • [ 92-81-9 ]
  • 29
  • [ 16726-19-5 ]
  • palladium [ No CAS ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
  • 30
  • [ 20378-05-6 ]
  • palladium [ No CAS ]
  • [ 3295-64-5 ]
  • [ 92-81-9 ]
  • [ 1658-08-8 ]
  • 31
  • [ 92-81-9 ]
  • [ 52853-40-4 ]
  • N-[(2,4-diaminopteridin-6-yl)methyl]-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
~ 10% EXAMPLE 3; Preparation of 2,4-Diamino-6-(9,10-dihydroacridin-9-yl)methylpteridine (Formula I: Ar=6-(2,4-diaminopteridine); X=N; W=CH2; Z=CH2; m=n=0).;Raney Ni (1 g) was added to a solution of acridine (1 g, 5.58 mmol) in EtOH (20 mL), and the mixture was shaken under a hydrogen atmosphere (50 psi) for 2 days. Additional EtOH (200 mL) was added, and the Ni catalyst was removed by filtration. Evaporation of filtrate and recrystallization of the residue from MeOH afforded colorless needles of 5,10-dihydroacridine (0.7 g, 70% yield); mp 169-170 C. A portion of this material (0.224 g, 1.18 mmol) was dissolved in dry THF (10 mL) under N2, and the solution was cooled to 0 C., and NaH (50% oil suspension containing 0.119 g, 4.7 mmol) was added in small portions with magnetic stirring After 10 min, 2,4-diamino-6-bromomethylpteridine hydrobromide (0.100 g, 0.392 mmol) was added slowly with continued stirring, and the reaction mixture was allowed to warm to room temperature and stirred overnight. Excess sodium hydride was destroyed with a small drops of AcOH, and the solvents were removed by rotary evaporation. Flash chromatography of the residue on silica gel with 9:1 ChCl3-MeOH as the eluent afforded the title compound, 2,4-diamino-6-(9,10-dihydroacridin-9-yl)methylpteridine, as a yellow-brown solid (ca. 10% yield); mp>250 C. dec. MS (FAB m/z (M+1)=370.1785.
  • 32
  • scrap tire [ No CAS ]
  • [ 92-81-9 ]
  • [ 92-83-1 ]
  • [ 611-61-0 ]
  • [ 2350-89-2 ]
YieldReaction ConditionsOperation in experiment
With air at 650 - 850℃; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;
  • 33
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  • [ 3295-64-5 ]
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  • [ 1658-08-8 ]
  • 34
  • [ 110166-26-2 ]
  • [ 92-81-9 ]
  • [ 321-64-2 ]
YieldReaction ConditionsOperation in experiment
1: 79% 2: 11% With sodium hydroxide; aluminum nickel In 1,4-dioxane for 3h; Irradiation;
1: 26% 2: 60% With sodium hydroxide; aluminum nickel In 1,4-dioxane for 3h; Heating;
  • 35
  • [ 92-81-9 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: LDA 2: DDQ 3: H2O2 / alkaline aq. solution / chemiluminescent reaction
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: iron(II) chloride; di-tert-butyl peroxide; ethyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 36
  • [ 92-81-9 ]
  • trans,syn,trans-perhydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 250 °C / 15200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: 80 percent / H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr

  • 37
  • [ 92-81-9 ]
  • (4aα,8aα,9aβ,10aα)-Tetradecahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 250 °C / 15200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: 80 percent / H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr

  • 38
  • [ 92-81-9 ]
  • (4aα,8aα,9aα,10aβ)-Tetradecahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 250 °C / 15200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: 80 percent / H2 / Pd-Al2O3 / decahydronaphthalene / 0.17 h / 150 °C / 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / 1 h / 150 - 200 °C / 15200 - 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr
Multi-step reaction with 2 steps 1: H2 / Pd-Al2O3 / decahydronaphthalene / 150 - 200 °C / 15200 - 53200 Torr 2: H2 / Pd-Al2O3 / decahydronaphthalene / 1 h / 150 °C / 53200 Torr

  • 39
  • [ 92-81-9 ]
  • [ 106916-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 54 percent / manganese(III) acetate, 2,4-pentanedione / acetic acid / 0.02 h / Heating 2: 14 percent / manganese(III) acetate / acetic acid / 0.02 h / Heating
  • 40
  • [ 92-81-9 ]
  • 9<i>H</i>-acridine-10-carboxylic acid-(2-diethylamino-ethyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene 2: benzene
Multi-step reaction with 2 steps 1: pyridine; toluene 2: benzene
  • 41
  • [ 92-81-9 ]
  • 9<i>H</i>-acridine-10-carboxylic acid-(2-diethylamino-ethylamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; toluene 2: benzene
  • 42
  • [ 74-96-4 ]
  • [ 92-81-9 ]
  • [ 10336-23-9 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; Inert atmosphere; Stage #2: ethyl bromide In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
With n-butyllithium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: ethyl bromide In tetrahydrofuran; hexane at 0 - 20℃; Schlenk technique; Inert atmosphere;
  • 43
  • [ 108-86-1 ]
  • [ 92-81-9 ]
  • [ 10336-24-0 ]
YieldReaction ConditionsOperation in experiment
77% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h; Schlenk technique; Inert atmosphere;
76% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h; Inert atmosphere;
With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h;
With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 120℃; for 0.5h; Inert atmosphere;

  • 44
  • [ 92-81-9 ]
  • [ 501-53-1 ]
  • [ 1252763-55-5 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: benzyl chloroformate In tetrahydrofuran; hexane at -5 - 20℃; Schlenk technique; Inert atmosphere;
90% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; Inert atmosphere; Stage #2: benzyl chloroformate In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
90% Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: benzyl chloroformate In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
  • 45
  • [ 62-53-3 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(II) oxide 2: sodium / butan-1-ol / 110 °C
Multi-step reaction with 3 steps 1: copper(I) oxide; copper; potassium carbonate / ethyl methyl ether / 5 h / 140 °C 2: sulfuric acid / 4 h / 100 °C 3: borane-THF / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
Multi-step reaction with 3 steps 1: copper(I) oxide; 4-methyl-morpholine / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2: polyphosphoric acid / 3 h / 100 °C 3: borane-THF / tetrahydrofuran / 80 °C / Inert atmosphere
  • 46
  • [ 118-91-2 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(II) oxide 2: sodium / butan-1-ol / 110 °C
Multi-step reaction with 3 steps 1: copper(I) oxide; copper; potassium carbonate / ethyl methyl ether / 5 h / 140 °C 2: sulfuric acid / 4 h / 100 °C 3: borane-THF / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
  • 47
  • [ 937-32-6 ]
  • [ 92-81-9 ]
  • [ 1334412-03-1 ]
YieldReaction ConditionsOperation in experiment
7% With triethylamine at 20℃; for 16h;
  • 48
  • [ 91-40-7 ]
  • [ 92-81-9 ]
  • 49
  • [ 104-92-7 ]
  • [ 92-81-9 ]
  • 10-(4-methoxyphenyl)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h;
  • 50
  • [ 92-81-9 ]
  • [ 75-52-5 ]
  • [ 260-94-6 ]
  • [ 22409-46-7 ]
YieldReaction ConditionsOperation in experiment
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen at 60℃; for 18h;
  • 51
  • [ 92-81-9 ]
  • [ 106-38-7 ]
  • [ 91222-25-2 ]
YieldReaction ConditionsOperation in experiment
57% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h;
  • 52
  • [ 92-81-9 ]
  • [ 92-66-0 ]
  • [ 366015-79-4 ]
YieldReaction ConditionsOperation in experiment
52% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h;
  • 53
  • [ 92-81-9 ]
  • [ 106-94-5 ]
  • [ 18448-45-8 ]
YieldReaction ConditionsOperation in experiment
54% With n-butyllithium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
  • 54
  • [ 92-81-9 ]
  • NaOBut [ No CAS ]
  • [ 92-66-0 ]
  • (t-Bu)3P [ No CAS ]
  • [ 366015-79-4 ]
YieldReaction ConditionsOperation in experiment
70% In toluene S.1.2 Synthesis of 10-(biphenyl-4-yl)-9,10-dihydroacridine of Reaction Scheme 1 Synthesis Example 1-2 Synthesis of 10-(biphenyl-4-yl)-9,10-dihydroacridine of Reaction Scheme 1 The obtained 9,10-dihydroacridine (11.8 g, 65.2 mmol) and 4-bromobiphenyl (18.2 g, 78.2 mmol) were dissolved in toluene (500 mL). Then, Pd2(dba)3 (1.4 g, 1.3 mmol) was added thereto under a nitrogen atmosphere. Then, NaOBut (9.4 g, 97.8 mmol) was added thereto, and (t-Bu)3P (1.6 ml, 2.6 mmol) was introduced to the resultant solution. The resultant mixture was reflux-stirred for 5 hours. The completion of the reaction was identified by a TLC. After the reaction was completed, the mixture was cooled to room temperature. The resultant solution was poured onto a thin silica pad so as to perform a short chromatography, and then was washed with MC. The filtrate was evaporated under a reduced pressure to remove the solvent. The residue was then purified by silica gel column chromatography (methylene chloride/n-hexane (1/10)) to obtain 10-(biphenyl-4-yl)-9,10-dihydroacridine compound (pale yellow solid, 15.3 g, yield 70%). 1H NMR: 3.8 (s, 2H), 6.4 (t, 2H), 6.6 (m, 4H), 6.9 (m, 4H), 7.5 (m, 5H), 7.8 (t, 2H).
  • 55
  • [ 92-81-9 ]
  • [ 79-37-8 ]
  • [ 34756-36-0 ]
YieldReaction ConditionsOperation in experiment
15% Stage #1: acridine; oxalyl dichloride In tetrahydrofuran for 4h; Reflux; Stage #2: With aluminum (III) chloride In chloroform for 23h; Reflux; 4.2.6. 4-Phenyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (9) General procedure: Dihydroquinoline 8 (1.04 g, 5.02 mmol) in anhydrous THF (6 mL) was added portion wise over 30 min to a refluxing solution of oxalyl chloride (1.27 g, 873 μL, 10.0 mmol) in anhydrous THF (4 mL). The reaction mixture was heated at reflux for 3.5 h before the solvent was removed by rotary evaporation. The dark residue was dissolved in anhydrous CHCl3 (30 mL) and heated at reflux. AlCl3 (2.01 g, 15.1 mmol) was added portion wise over 5 h and the solution was heated at reflux for a further 18 h. The solvent was once again removed by rotary evaporation, the residue was cooled on ice, concentrated HCl (10 mL) was added, followed by H2O (10 mL) and CHCl3 (50 mL). The phases were separated and the organic layer was washed with H2O (2×50 mL), dried over MgSO4, filtered and the solvent removed by rotary evaporation. The resulting solid was purified by flash chromatography (100% DCM) to yield 9 as dark red crystals (15.7 mg, 1%).
  • 56
  • 10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroacridine [ No CAS ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
44 mg With water In dichloromethane
With water In hexane
0.14 g With water; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 57
  • [ 92-81-9 ]
  • [ 24424-99-5 ]
  • [ 1581699-83-3 ]
YieldReaction ConditionsOperation in experiment
83% With dmap In acetonitrile at 0 - 30℃; for 24h;
80% With dmap In acetonitrile at 20℃; for 11h; tert-Butyl acridine-10(9H)-carboxylate (1c): A two-necked 20-mL round-bottomed flask equipped witha magnetic stirring bar was charged with acridone (195 mg, 1.00 mmol), and THF (2.5 mL). To thesolution was added BH3THF (1.08 M in THF, 1.3 mL, 1.4 mmol) at room temperature. The reactionmixture was heated to reflux for 4 h, after which time TLC (hexanes-EtOAc = 3:1) indicated completeconsumption of acridone. The reaction was quenched with brine and 2 M aqueous NaOH, and the mixturewas extracted with Et2O three times. The combined organic extracts were washed with saturated aqueousNaHCO3, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated underreduced pressure to afford the crude dihydroacridine as a colorless solid, which was used for the nextreaction without further purification.A 50-mL round-bottomed flask equipped with a magnetic stirring bar was charged with dihydroacridine,Boc2O (766 mg, 3.51 mmol), and MeCN (3.3 mL). To the solution was added DMAP (203 mg, 1.66mmol) at 0 °C. The solution was stirred for 11 h at room temperature, after which time TLC(hexanes-EtOAc = 9:1) indicated complete consumption of dihydroacridine. The reaction was dilutedwith Et2O. The mixture was washed with saturated aqueous NH4Cl and brine, dried over anhydroussodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gelcolumn chromatography (hexanes-EtOAc = 9:1) to afford N-Boc-dihydroacridine 1c (226 mg, 0.803mmol, 80%) as colorless crystals; Rf = 0.47 (hexanes-EtOAc = 9:1); IR (neat, cm-1): 1706, 1476, 1328,1269, 1253, 1151, 760; 1H NMR (400 MHz, CDCl3): " 7.63 (d, 2H, J = 8.0 Hz), 7.36-7.17 (m, 4H), 7.12(d, 2H, J = 7.2 Hz), 3.80 (s, 2H), 1.54 (s, 9H); 13C NMR (125 MHz, CDCl3): " 152.5, 138.8, 133.0, 126.9,125.9, 125.04, 124.96, 33.8, 28.2, 27.9; HRMS (ESI): Calcd. for C14H12NO2 [(M-t-Bu)+], 226.0863;Found: 226.0878; Anal. Calcd for C18H19NO2: C, 76.84; H, 6.81; N, 4.98; Found: C, 76.64; H, 6.83; N,5.01.
226 mg With dmap In acetonitrile at 0 - 20℃; for 11h; Inert atmosphere; General procedure: A two-necked 20-mL round-bottomed flask equipped with a magnetic stirring bar was charged with acridone 11 (195 mg, 1.00 mmol), and THF (2.5 mL). To the solution was added BH3*THF (1.08 M in THF, 1.3 mL, 1.4 mmol) at room temperature. The reaction mixture was heated at reflux for 4 h. The reaction was quenched with brine and 2 M aqueous NaOH, and the mixture was extracted with ether three times. The combined organic extracts were washed with saturated aqueous NaHCO3, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to afford the crude dihydroacridine 12 as a colorless solid, which was used to the next reaction without further purification. A 50-mL round-bottomed flask equipped with a magnetic stirring bar was charged with 12, Boc2O (766 mg, 3.51 mmol), and MeCN (3.3 mL). To the solution was added DMAP (203 mg, 1.66 mmol) at 0°C and stirring was continued for 11 h at room temperature. The reaction was diluted with ether. The mixture was washed with saturated aqueous NH4Cl and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to leave the residue, which was purified by silica gel column chromatography(hexanes-EtOAc= 9 : 1) to afford 13 (226 mg, 0.803 mmol, 80%). mp 97.4-98.9 °C, colorless crystals; Rf=0.47 (Silica gel,hexanes-EtOAc= 9 : 1); IR (neat) cm-1: 1706, 1476, 1328, 1269,1253, 1151, 760; 1H-NMR (400 MHz, CDCl3) δ: 7.63 (d, 2H,J=8.0 Hz), 7.36-7.17 (m, 4H), 7.12 (d, 2H, J=7.2 Hz), 3.80 (s,2H), 1.54 (s, 9H); 13C-NMR (125 MHz, CDCl3) δ: 152.5, 138.8,133.0, 126.9, 125.9, 125.04, 124.96, 33.8, 28.2, 27.9; HR-MS(ESI) Calcd for C14H12NO2 [(M-t-Bu+ 2H)+] 226.0863, Found:226.0878.
  • 58
  • [ 37686-36-5 ]
  • [ 92-81-9 ]
  • 10-(selenophen-2-yl)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate for 2h; Reflux; 2-1.ii (ii) Synthesis of Compound (2) 10383] 6.78 g (26.4 mmol) of 2-iodoselenophene and 3.99 g (22 mmol) of 9,-lO-dihydroacridine are heated and refluxed for 2 hours in 45 ml of anhydrous toluene under presence of 5 mol % of Pd(dba)2, 5 mol % of P(tBu)3, and 2.33 g (24.2 mmol) of NaOtl3u. A product obtained therefrom was separated and purified through silica gel column chromatography (a volume ratio of toluene:hexane=1 :4) to obtain 2.57 g of 1 0-(selenophen-2-yl)-9, 10-dihydroacridine (Yield: 3 8%).
  • 59
  • [ 92-81-9 ]
  • terbium(III) chloride [ No CAS ]
  • 3C13H10N(1-)*Tb(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: acridine With n-butyllithium In toluene at 0℃; Stage #2: terbium(III) chloride In tetrahydrofuran; toluene at 0℃; 2 Ligand 4 (Edema 4) was used as a starting material.The reaction was carried out under anhydrous anaerobic protection.To a solution of 3.2 mmol of Cyanamine 4 in toluene was slowly added n-butyllithium (2 mL, 3.2 mmol) dropwise at 0 ° C and the mixture was stirred overnight.1.07mmol anhydrous terbium trichloride at the same time do the drying.The next day, to maintain 0 ° C, to the mixed solution was added mixed with terbium trichloride toluene suspension, the feed to be slow, a small amount of tetrahydrofuran was added, the mixed solution was stirred overnight.The volume of the solution is reduced to half and the supernatant is taken.Carbon dioxide was introduced into the yellow supernatant at 0 ° C., the color of the solution gradually faded off, and the carbon dioxide channel was closed after 45 min. The solution was further stirred overnight.The next day the mixture precipitated carbamate terbium salt, the yield of about 30%.
  • 60
  • [ 40102-90-7 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 1-(acridin-10(9H)-yl)ethan-1-one With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 24h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;
64% With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; 9 Example 9, wherein the amide substrate is as follows: Under argon atmosphere,Firstly, NaOH and triethylboron are stirred to form a transparent clear solution at room temperature.The concentration is 1M/L;Then,The above triethylboron solution was successively treated with 10umol (2mol%),Amide substrate 5mmol,Triethoxysilane or polymethylhydrogensiloxane 15mmol,MTBE 2mL added to the 10mL sealed tube,It is heated and stirred in an 80°C oil bath for 6 hours.The reaction is over,Exposing the reaction to air quenching,The amine product is then separated directly by column chromatography.According to the results of column chromatography separation, when using triethoxysilane or polymethylhydrogensiloxane (PMHS),The yield of the target product was:
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
  • 61
  • [ 92-81-9 ]
  • [ 589-87-7 ]
  • (10-(4-bromophenyl)-9,10-dihydroacridine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; rac-diaminocyclohexane; sodium t-butanolate In 1,4-dioxane at 101℃; for 6h; Inert atmosphere; 4 Preparation of compound a4 9,10-dihydroacridine (9.9 g, 54.5 mmol),4-bromoiodobenzene (17 g, 60 mmol), 1,2-cyclohexanediamine(0.63g, 5.5mmol),Sodium tert-butoxide (10.5 g, 109 mmol) and cuprous iodide (0.21 g, 1.1 mmol) were placed in a 250 mL single-necked flask.Under the protection of nitrogen,Add anhydrous 1,4-dioxane (100 mL),Stir at 101 ° C for 6 hours under reflux. The reaction system is cooled to room temperature, and the dichloromethane is separated and separated.The organic layer was dried over anhydrous magnesium sulfate and filtered.Concentrated under reduced pressure,Column chromatography (eluent is a 1:4 mixture of dichloromethane and petroleum ether),Obtaining 12.8 g of compound a4 (10-(4-bromophenyl)-9,10-dihydroacridine),The yield was 70%.
  • 62
  • [ 92-81-9 ]
  • [ 578-95-0 ]
YieldReaction ConditionsOperation in experiment
99% With tert.-butylhydroperoxide; 0.5C34H18N16(4-)*2H2O*2Cu(1+)*C3H7NO In water at 20℃; for 4h; Sonication;
93% With tert.-butylhydroperoxide; 2C36H20N2O8(4-)*5Co(2+)*2HO(1-)*4H2O*6C3H7NO In water at 20℃; for 9h; Sonication; regioselective reaction;
92% With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Irradiation;
62.2 %Chromat. With oxygen In acetone for 12h; Irradiation;

  • 63
  • [ 92-81-9 ]
  • [ 125369-78-0 ]
  • (2Z,4E)-2-(4-(acridin-10(9H)-yl)phenyl)-5-phenylpenta-2,4-dienenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 24h; Inert atmosphere; Reflux; 2.2.2. Synthesis of 1b To a mixture of 9,10-dihydroacridine (312 mg, 1.76 mmol), Pd(OAc)2 (9.0 mg, 0.04 mmol), P(t-Bu)3 (1.94 mg, 0.01 mmol), and Cs2CO3 (1.043 g, 3.20 mmol) in dry toluene (60 mL) was added 4 (496 mg, 1.60 mmol). The mixture was refuxed under nitrogen until the reaction was completed (24 h). Then, the reaction mixture was cooled to room temperature and filtered. The solvent was removed under vacuum. The residue was purified by silica-gel flash chromatography(hexane/dichloromethane, 3/1) to give 1b as a light yellow solid (426 mg, 65%). m. p. 250-251 °C; 1H NMR (400 MHz, CDCl3):δ=7.88 (d, J=8.4 Hz, 2H), 7.59 (d, J=7.0 Hz, 2H), 7.55-7.35 (m,7H), 7.16 (d, J=7.0 Hz, 2H), 7.09 (d, J=14.6 Hz, 1H), 7.00-6.93 (m,2H), 6.91-6.85 (m, 2H), 6.22 (d, J=8.1 Hz, 2H), 4.23 ppm (s, 2H); 13CNMR (100 MHz, CDCl3): δ=142.4 (CH), 142.0 (CH), 135.7 (C), 133.2(C), 132.1 (CH), 129.8 (CH), 129.0 (CH), 128.5 (CH), 128.0 (CH), 127.7(CH), 126.7 (CH), 125.1 (CH), 121.0 (C), 120.8 (C), 116.8 (CH), 113.9(CH), 112.3 (C), 31.9 ppm (CH2), two overlapping Ar-C resonance;HRMS (ESI): m/z calcd for C30H21N2+: 409.1699 [M-H] +; found:409.1694.
  • 64
  • [ 92-81-9 ]
  • N-(1-adamanty)-3,3-bis(trimethylsilyl)-1-aza-2λ2-silacyclopentane [ No CAS ]
  • C32H48N2Si3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In n-heptane at 150℃; for 1h; Sealed tube;
  • 65
  • [ 1207-69-8 ]
  • [ 92-81-9 ]
  • [ 578-95-0 ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 40% With phosphorus; water; potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere; Reaction of 9-chloroacridine with red phosphorus/KOH/DMSO(H2O) system A mixture of red phosphorus (0.65 g, 20.97 mmol), 9-chloroacridine(0.744 g, 3.49 mmol), KOH · 0.5H2O (1.50 g,11.77 mmol), and H2O (0.125 mL, 10.9 mmol) inDMSO (16 mL) was stirred for 3 h at 100°C in an argon atmosphere. The reaction mixture was cooled to ambient temperature, filtered using a Schott sintereddisc filter funnel, and DMSO was removed under reduced pressure. The resultant residue was washed with water (3 × 15-20 mL), and dried under reducedpressure to give 0.719 g of a mixture of products (dark brown powder). The powder was washed with chloroform(3 × 10 mL) and filtered off. The chloroform was removed to give 0.32 g (51%) of 9,10-dihydroacridine as a cream-colored powder, mp 169-170°C. 1H NMR (CDCl3, δ, ppm): 4.04 (s, 2H, CH2),5.93 (br s, 1H, NH), 6.65 (d, 2H, Ar), 6.83 (t, 2H, Ar),7.08 m (4H, Ar).13C NMR (CDCl3, δ, ppm): 31.3 (C9), 113.4 (C4,5),120.0 (C12), 120.6 (C2,7), 127.0 (C1,8), 128.6 (C3,6),140.2 (C11).For C13H11N anal. calcd. (%): C, 86.15; H 6.12.Found (%): C, 86.10; H, 6.23.Acridone (0.27 g, 40%) as a crystalline matter was isolated from the residue and characterized by GC-MS and 1H NMR.
  • 66
  • [ 92-81-9 ]
  • 5-(cyano)dibenzothiophenium triflate [ No CAS ]
  • C14H10N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With caesium carbonate In dichloromethane at 20℃; for 3h; Inert atmosphere;
  • 67
  • [ 6582-52-1 ]
  • [ 260-94-6 ]
  • [ 92-81-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; aniline; In water; at 160 - 180℃; In a series of experiments, the amount of aqueous 30% hydrochloric acid required in each case to achieve the desired protonation level (see table 3 below) was added to a 2,2?-MDA solution in aniline preheated to 100.0 C. The 2,2?-MDA concentration in each of the individual experiments was 1.0% by mass; in addition, the solutions contained octadecane as an internal standard for gas chromatography (GC) analysis. The resulting mixture was transferred as quickly as possible by means of a peristaltic pump to a Buechi glass autoclave preheated to 120.0 C. and heated to the reaction temperature envisaged (see table 3). On attainment of the desired reaction temperature, the first sample was taken (time=zero). In order to monitor the progress of the reaction, further samples were taken after 30, 60, 120 and 240 minutes and analyzed by means of GC analysis. Reaction conditions and experimental results are collated in table 3 below. It is found that, with rising temperature and rising hydrochloric acid concentration, the formation of the acridine and acridane secondary components from 2,2?-MDA occurs to an increased degree.
With hydrogenchloride; In water; at 100 - 170℃; for 4h;Autoclave; General procedure: In a series of experiments, the amount of aqueous 30% hydrochloric acid required in each case to achieve the desired protonation level (see table 3 below) was added to a 2,2?-MDA solution in aniline preheated to 100.0 C. The 2,2?-MDA concentration in each of the individual experiments was 1.0% by mass; in addition, the solutions contained octadecane as an internal standard for gas chromatography (GC) analysis. The resulting mixture was transferred as quickly as possible by means of a peristaltic pump to a Blichi glass autoclave preheated to 120.0 C. and heated to the reaction temperature envisaged (see table 3). On attainment of the desired reaction temperature, the first sample was taken (time=zero). In order to monitor the progress of the reaction, further samples were taken after 30, 60, 120 and 240 minutes and analyzed by means of GC analysis.
  • 68
  • [ 92-81-9 ]
  • C13H7(2)H4N [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;
  • 69
  • [ 50-00-0 ]
  • [ 92-81-9 ]
  • [ 4217-54-3 ]
YieldReaction ConditionsOperation in experiment
88% With sodium cyanoborohydride; acetic acid In water
  • 70
  • [ 92-81-9 ]
  • [ 17024-12-3 ]
  • [ 106-45-6 ]
  • 10-(phenanthren-9-yl)-9-(p-tolylthio)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: acridine; 9-iodo-phenanthrene With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h; Stage #2: para-thiocresol In ethanol at 20℃; for 24h; 2.1. Preparation of B1 and B2 General procedure: Compounds B1 and B2 were synthesized as described in ourprevious study [9]. To a solution of the sulfenylation of 9,10-dihydroacridines (500 mg) and iodobenzene (281.4 mg) intoluene (10 mL) were added tri-tert-butylphosphine (19.4 mg),palladium acetate (30 mg) and potassium tert-butoxide (403 mg).The reaction mixture was stirred and reacted at 130 C for 30 min.After reaction, the solvents was removed under reduced pressureand then a solution of thiophenol (50 mg) in EtOH (2 mL) wereadded to the reaction residue. The mixture was stirred under atmosphereat room temperature for 24 h. The resulting mixture wasthen concentrated under reduced pressure. After removal of thesolvent, the residue was then purified by flash column chromatographyon silica gel with a mixture solvent of petroleum etherand ethyl acetate 4:1 to give the desired B1 with 80% yields. Thesynthesis of B2 was achieved by replacing 9-iodophenanthrenelwith iodobenzene in the first step of the synthesis.
  • 71
  • [ 92-81-9 ]
  • [ 591-50-4 ]
  • [ 106-45-6 ]
  • 10-phenyl-9-(p-tolylthio)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: acridine; iodobenzene With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 130℃; for 0.5h; Stage #2: para-thiocresol In ethanol at 20℃; for 24h; 2.1. Preparation of B1 and B2 Compounds B1 and B2 were synthesized as described in ourprevious study [9]. To a solution of the sulfenylation of 9,10-dihydroacridines (500 mg) and iodobenzene (281.4 mg) intoluene (10 mL) were added tri-tert-butylphosphine (19.4 mg),palladium acetate (30 mg) and potassium tert-butoxide (403 mg).The reaction mixture was stirred and reacted at 130 C for 30 min.After reaction, the solvents was removed under reduced pressureand then a solution of thiophenol (50 mg) in EtOH (2 mL) wereadded to the reaction residue. The mixture was stirred under atmosphereat room temperature for 24 h. The resulting mixture wasthen concentrated under reduced pressure. After removal of thesolvent, the residue was then purified by flash column chromatographyon silica gel with a mixture solvent of petroleum etherand ethyl acetate 4:1 to give the desired B1 with 80% yields. Thesynthesis of B2 was achieved by replacing 9-iodophenanthrenelwith iodobenzene in the first step of the synthesis.
  • 72
  • [ 92-81-9 ]
  • [ 165612-94-2 ]
  • 10-(bis(perfluorophenyl)boraneyl)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.1% In dichloromethane for 24h;
  • 73
  • [ 92-81-9 ]
  • [ 2720-03-8 ]
  • 10-(bis(perfluorophenyl)boraneyl)-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.1% Stage #1: acridine With sodium hydride In tetrahydrofuran Stage #2: bis(pentafluorophenyl)boron chloride In dichloromethane for 16h;
  • 74
  • [ 92-81-9 ]
  • [ 638-45-9 ]
  • C19H23N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: 1-Iodohexane In tetrahydrofuran; hexane at 0 - 20℃; Schlenk technique; Inert atmosphere;
  • 75
  • [ 92-81-9 ]
  • [ 620-05-3 ]
  • [ 87742-33-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: acridine With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: iodomethylbenzene In tetrahydrofuran; hexane at 0 - 20℃; Schlenk technique; Inert atmosphere;
  • 76
  • [ 92-81-9 ]
  • C20H19N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 77
  • [ 92-81-9 ]
  • n-butyl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 78
  • [ 92-81-9 ]
  • tert-butyl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 79
  • [ 92-81-9 ]
  • benzyl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 80
  • [ 92-81-9 ]
  • phenyl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 81
  • [ 92-81-9 ]
  • allyl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 82
  • [ 92-81-9 ]
  • (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-yl 2-diazo-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 83
  • [ 92-81-9 ]
  • 2-diazo-N,N-diethyl-4-(10-methyl-9,10-dihydroacridin-9-yl)-3-oxobutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 84
  • [ 92-81-9 ]
  • 1-diazo-3-(10-methyl-9,10-dihydroacridin-9-yl)-1-(methylsulfonyl)propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 1.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: methanesulfonic acid; oxygen / dichloromethane / 48 h / 20 °C / 760.05 Torr
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