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Chemical Structure| 719-54-0
Chemical Structure| 719-54-0
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Product Details of [ 719-54-0 ]

CAS No. :719-54-0 MDL No. :MFCD00005024
Formula : C14H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :XUVKSPPGPPFPQN-UHFFFAOYSA-N
M.W : 209.24 Pubchem ID :69751
Synonyms :

Calculated chemistry of [ 719-54-0 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.07
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.98
TPSA : 22.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 2.32
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.74
Solubility : 0.0377 mg/ml ; 0.00018 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.12 mg/ml ; 0.000575 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.85
Solubility : 0.00295 mg/ml ; 0.0000141 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 719-54-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 719-54-0 ]

* 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 [ 719-54-0 ]

[ 719-54-0 ] Synthesis Path-Downstream   1~72

  • 1
  • [ 4217-54-3 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
100% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In acetonitrile at 80℃; for 40h;
96% With 2-fluoren-9-ylidene-malononitrile; oxygen In acetonitrile at 60℃; for 24h;
94% With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 18h; Irradiation;
94% With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 18h; Sealed tube; 1; 2; 3; 4; 5; 6; 7; 8; 9 Example 1: Preparation of 10-methylacridine-9(10H)-one (formula (2-1)) In a 15 mL sealed tube equipped with a magnetic stir bar,Add 1 mmol of 10-methyl-9,10-dihydroacridine (formula (1-1))And 0.01 mmol of DDQ,Replace the air inside the tube with oxygen,After sealing the bottle with a rubber stopper,Insert the oxygen balloon,Add 0.05 mmol of TBN to the sealed tube.0.2 mmol of acetic acid and 5 mL of 1,2-dichloroethane,After 18h reaction at room temperature under the illumination of 18W blue LED lamp,Evaporate the solvent under reduced pressure.Perform column chromatography separation,a mixture of ethyl acetate/petroleum ether in a volume ratio of 1:50 as an eluent,Collect the eluate containing the target compound,Evaporating the solvent gave the product 10-methylacridine-9(10H)-one.The isolated yield was 94%.
91% Stage #1: 9,10-dihydro-10-methylacridine With tetra-O-acetyl riboflavin; oxygen In acetonitrile for 0.0333333h; Green chemistry; Stage #2: In acetonitrile at 20℃; for 10h; 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).
56% With air In 1,2-dichloro-ethane at 20℃; for 3h; UV-irradiation; 4.1. Typical procedure for the preparation of 9H-Xanthen-9-one(2a) General procedure: A 15-mL Schlenk tube equipped with a magnetic stirrer bar was charged with xanthene (1a; 36.4 mg, 0.2 mmol) and DMSO (2 mL). The Schlenk tube was placed in a dark box and illuminated with 6Wblue LED (380-385 nm). The mixture was stirred vigorously at room temperature in air until the reaction was complete (GC). The mixture was then concentrated on a rotary evaporator, and the residue was purified by column chromatography (silica gel, PE-EtOAc) to 2a: white solid.
55 % Spectr. In acetonitrile at 12℃; for 0.5h; Irradiation; photoionization;
bei der Oxydation an der Luft;
With oxygen In acetonitrile for 25h; Irradiation;
55 % Spectr. With oxygen In acetonitrile at 12℃; for 0.5h; Irradiation;
With trans-dioxomanganese(V) meso-tetrakis(pentafluorophenyl)porphyrin anion In chloroform-d1 at 25℃;
With manganese(III) 2,3,7,8,12,13,17,18-octakis(4-tert-butylphenyl)corrolazine; oxygen In benzonitrile at 20℃; UV-irradiation;
With 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinatomanganese-(III) acetate; oxygen In acetonitrile at 298℃; Irradiation;
With C14H32ClCrN4O2(1+)*Cl(1-) In acetonitrile at -20.16℃;
19 %Spectr. With di-tert-butyl peroxide; ethyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate; iron(II) chloride In dichloromethane at 20℃; for 48h;

Reference: [1]Zhang, Bo; Cui, Yuxin; Jiao, Ning [Chemical Communications, 2012, vol. 48, # 37, p. 4498 - 4500]
[2]Jiang, Hong; Liu, You-Cheng; Li, Jing; Wang, Guan-Wu; Wu, Yun-Dong; Wang, Quan-Ming; Mak, Thomas C. W. [Chemical Communications, 2002, # 8, p. 882 - 883]
[3]Pan, Decheng; Wang, Yiqing; Li, Meichao; Hu, Xinquan; Sun, Nan; Jin, Liqun; Hu, Baoxiang; Shen, Zhenlu [Synlett, 2019, vol. 30, # 2, p. 218 - 224]
[4]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN109336813, 2019, A Location in patent: Paragraph 0025-0042
[5]Chinchilla, Rafael; Torregrosa-Chinillach, Alejandro [Molecules, 2021, vol. 26, # 4]
[6]Zhou, Jiacheng; Li, Meichao; Li, Tianci; Li, Chunmei; Hu, Xinquan; Jin, Liqun; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu [Tetrahedron, 2021, vol. 82]
[7]Shukla, Deepak; Rege, Francis de; Wan, Peter; Johnston, Linda J. [Journal of Physical Chemistry, 1991, vol. 95, # 25, p. 10240 - 10246]
[8]Pictet; Patry [Chemische Berichte, 1902, vol. 35, p. 2536]
[9]Fukuzumi, Shunichi; Ishikawa, Masashi; Tanaka, Toshio [Journal of the Chemical Society. Perkin transactions II, 1989, p. 1037 - 1046]
[10]Shukla, Deepak; Rege, Francis de; Wan, Peter; Johnston, Linda J. [Journal of Physical Chemistry, 1991, vol. 95, # 25, p. 10240 - 10246]
[11]Lee, Jung Yoon; Lee, Yong-Min; Kotani, Hiroaki; Nam, Wonwoo; Fukuzumi, Shunichi [Chemical Communications, 2009, # 6, p. 704 - 706]
[12]Jung, Jieun; Ohkubo, Kei; Prokop-Prigge, Katharine A.; Neu, Heather M.; Goldberg, David P.; Fukuzumi, Shunichi [Inorganic Chemistry, 2013, vol. 52, # 23, p. 13594 - 13604]
[13]Jung, Jieun; Ohkubo, Kei; Goldberg, David P.; Fukuzumi, Shunichi [Journal of Physical Chemistry A, 2014, vol. 118, # 32, p. 6223 - 6229]
[14]Devi, Tarali; Lee, Yong-Min; Jung, Jieun; Sankaralingam, Muniyandi; Nam, Wonwoo; Fukuzumi, Shunichi [Angewandte Chemie - International Edition, 2017, vol. 56, # 13, p. 3510 - 3515][Angew. Chem., 2017, vol. 129, # 13, p. 3564 - 3569]
[15]Li, Weiyu; Xu, Hao; Zhou, Lei [Organic and Biomolecular Chemistry, 2021, vol. 19, # 25, p. 5649 - 5657]
  • 2
  • [ 719-54-0 ]
  • [ 4217-54-3 ]
YieldReaction ConditionsOperation in experiment
86% With dimethylsulfide borane complex In tetrahydrofuran for 1h; Reflux;
82% With dimethylsulfide borane complex In tetrahydrofuran at 75 - 80℃; for 2h; Inert atmosphere;
81% With phenylphosphane at 140℃; for 24h;
81% With lithium aluminium tetrahydride In diethyl ether Inert atmosphere; Schlenk technique;
66% With sodium In pentan-1-ol Heating;
With i-Amyl alcohol; sodium
1.84 g With borane-THF In tetrahydrofuran for 2h; Reflux;

  • 3
  • [ 719-54-0 ]
  • [ 23663-77-6 ]
YieldReaction ConditionsOperation in experiment
80% With titanium tetrachloride; zinc In 1,4-dioxane for 72h; Heating;
With hydrogenchloride; ethanol; zinc
  • 4
  • [ 29897-82-3 ]
  • [ 26456-05-3 ]
  • [ 4217-54-3 ]
  • [ 719-54-0 ]
  • [ 100-52-7 ]
  • 10-Methyl-9-pyrrolidin-1-yl-acridinium; perchlorate [ No CAS ]
  • 5
  • [ 108-86-1 ]
  • [ 35472-56-1 ]
  • [ 719-54-0 ]
  • 6
  • [ 719-54-0 ]
  • [ 66228-30-6 ]
YieldReaction ConditionsOperation in experiment
75% With sodium borodeuteride In isopropyl alcohol at 80℃; for 14h;
57% With lithium aluminium deuteride In diethyl ether Inert atmosphere; Schlenk technique;
With lithium aluminium deuteride
With sodium borodeuteride In isopropyl alcohol at 80℃; for 14h; Yield given;
With lithium aluminium deuteride In diethyl ether
With lithium aluminium deuteride In diethyl ether
With lithium aluminium deuteride In diethyl ether
With lithium aluminium deuteride In diethyl ether
With lithium aluminium deuteride In diethyl ether

Reference: [1]Manring, Lewis E.; Peters, Kevin S. [Journal of the American Chemical Society, 1983, vol. 105, # 17, p. 5708 - 5709]
[2]Hübner, Olaf; Himmel, Hans-Jörg; Kaifer, Elisabeth; Walter, Petra; Wild, Ute [Chemistry - A European Journal, 2020, vol. 26, # 69, p. 16504 - 16513]
[3]Ostovic, Drazen; Roberts, Roger M. G.; Kreevoy, Mourice M. [Journal of the American Chemical Society, 1983, vol. 105, # 26, p. 7629 - 7631]
[4]Manring, Lewis E.; Peters, Kevin S. [Journal of the American Chemical Society, 1985, vol. 107, # 23, p. 6452 - 6458]
[5]Location in patent: experimental part Fukuzumi, Shunichi; Kotani, Hiroaki; Lee, Yong-Min; Nam, Wonwoo [Journal of the American Chemical Society, 2008, vol. 130, # 45, p. 15134 - 15142] Location in patent: experimental part Fukuzumi, Shunichi; Fujioka, Naofumi; Kotani, Hiroaki; Ohkubo, Kei; Lee, Yong-Min; Nam, Wonwoo [Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17127 - 17134]
[6]Lee, Jung Yoon; Lee, Yong-Min; Kotani, Hiroaki; Nam, Wonwoo; Fukuzumi, Shunichi [Chemical Communications, 2009, # 6, p. 704 - 706] Han, Yejee; Lee, Yong-Min; Mariappan, Mariappan; Fukuzumi, Shunichi; Nam, Wonwoo [Chemical Communications, 2010, vol. 46, # 43, p. 8160 - 8162]
[7]Location in patent: experimental part Fukuzumi, Shunichi; Kotani, Hiroaki; Prokop, Katharine A.; Goldberg, David P. [Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1859 - 1869]
[8]Yoon, Heejung; Lee, Yong-Min; Nam, Wonwoo; Fukuzumi, Shunichi [Chemical Communications, 2014, vol. 50, # 85, p. 12944 - 12946]
[9]Shi, Huatian; Lee, Hung Kay; Pan, Yi; Lau, Kai-Chung; Yiu, Shek-Man; Lam, William W. Y.; Man, Wai-Lun; Lau, Tai-Chu [Journal of the American Chemical Society, 2021, vol. 143, # 38, p. 15863 - 15872]
  • 7
  • [ 719-54-0 ]
  • [ 17435-19-7 ]
YieldReaction ConditionsOperation in experiment
98% With diphosphorus pentasulfide In N,N,N,N,N,N-hexamethylphosphoric triamide at 115℃; for 3.5h;
70% With tetraphosphorus decasulfide In pyridine at 80℃; for 8h;
Multi-step reaction with 2 steps 1: 96 percent / CH2Cl2 / 5 h / 0 °C 2: 61 percent / NaHS*H2O / acetonitrile
With Lawessons reagent In toluene for 8.17h; Inert atmosphere; Reflux; 1 Examples 1 Synthesis of Thioacridone Examples 1 Synthesis of Thioacridone[0056] A mixture of N-methyl acridone (250 m, 1.2 mmol) and Lawesson's reagent (540 mg, 1.34 mmol) in toluene (15 ml) was stirred under a nitrogen atmosphere for 10 minutes and then heated at reflux for 8 hours. On cooling to room temperature, the toluene was removed in vacuo and the thioacridone was recrystallised from DCM to give a dark orange solid. [0057] 1H NMR, IR and mass spec data were all in agreement with the literature (J. Pharm. Sci. 1971, 60, 1239). [0058] Fluorescence emission spectra of 10-methyl-9(10H)-thioacridone (N-methyl thioacridone) and 10-methyl-9(10H)-acridone (N-methylacridone) in 140 mM NaCl, 10 mM phosphate buffer pH 7.4 upon excitation at 405 nm, were obtained. The thioacridone concentration is 500 nM and the 10-methyl-9(10H)-acridone (N-methylacridone) concentration is 100 nM. Results are shown in Figure 1. [0059] In an attempt to generate acridone derivatives with enhanced fluorescence properties N-methyl thioacridone was generated and its fluorescence properties compared to N-methyl acridone. However, as can be seen from the fluorescence emission spectra, substitution of the carbonyl oxygen of acridone with sulphur, considerably attenuates the fluorescence of the molecule. The fluorescence emission intensity of the thioacridone is considerably less fluorescent than the corresponding methyl-acridone derivative.

  • 8
  • [ 17435-19-7 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; methylene blue In dichloromethane at -78℃; for 0.05h; Irradiation;
85% With oxygen; methylene blue In dichloromethane at -78℃; for 1h; Irradiation;
62.5% With mercury(II) perchlorate In dimethyl sulfoxide at 20℃;
  • 9
  • [ 772-54-3 ]
  • [ 26456-05-3 ]
  • [ 4217-54-3 ]
  • [ 719-54-0 ]
  • [ 100-52-7 ]
  • 9-(N-ethylbenzylamino)-10-methylacridinium perchlorate [ No CAS ]
  • 10
  • [ 34636-09-4 ]
  • [ 26456-05-3 ]
  • [ 4217-54-3 ]
  • [ 719-54-0 ]
  • [ 100-52-7 ]
  • 9-(Benzyl-isopropyl-amino)-10-methyl-acridinium; perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 73% 2: 2.9 % Spectr. 3: 14.6 % Chromat. 4: 13% With oxygen In acetonitrile for 24h; Ambient temperature;
  • 11
  • [ 83060-82-6 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
79% With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1.5h;
79% Stage #1: N,N-diethyll-2-(N-methylanilino)benzamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1.5h; Stage #2: With water; ammonium chloride In tetrahydrofuran; hexane at 0℃; regioselective reaction;
32% With trichlorophosphate In toluene for 10h; Heating;
  • 12
  • [ 26456-05-3 ]
  • [ 2905-56-8 ]
  • [ 4217-54-3 ]
  • [ 719-54-0 ]
  • [ 100-52-7 ]
  • 9-[Benzyl-(5-hydroxy-pentyl)-amino]-10-methyl-acridinium; perchlorate [ No CAS ]
  • 13
  • [ 578-95-0 ]
  • [ 74-88-4 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h;
97% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 18h; Inert atmosphere;
96% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0℃; for 4h; 10-Methylacridin-9(10H)-one (4d): A 30-mL flame-dried round-bottomed flask equipped with amagnetic stirring bar, a rubber septum, and a three-way stopcock was charged with acridone (398.0 mg,2.04 mmol) and anhydrous DMF (6.8 mL). To the solution was added NaH (164.0 mg, 4.10 mmol) at0 °C and the resulting mixture was stirred at room temperature for 30 min. To the resulting mixture was added MeI (255 μL, 4.10 mmol) dropwise at 0 °C. The resulting mixture was stirred for 4 h, after whichtime TLC (hexanes-EtOAc = 1:1) indicated complete consumption of acridone. The reaction mixture wasquenched with H2O, and the mixture was extracted with EtOAc three times. The combined organicextracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and filtered. The organicsolvents were removed under reduced pressure to give crude N-methylacridone 4d, which was purified byflash silica gel column chromatography (hexanes-EtOAc = 4:1) to afford N-methylacridone 4d (410.8 mg,1.96 mmol, 96%) as a pale yellow solid. The analytical data (IR, HRMS, 1H and 13C NMR) were identicalwith those reported in the literature.14 Rf = 0.44 (hexanes-EtOAc = 1:1).
96% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Schlenk technique; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 16h; Schlenk technique;
96% With benzyltrimethylammonium chloride; potassium hydroxide In tetrahydrofuran; water for 20h;
95% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h;
95% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h;
95% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 14h;
87% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h; 5.2.3. 10-Methylacridin-9(10H)-one (4) Intermediate 3 (1.5g, 7.7mmol) was dissolved in DMF (40mL) and NaH (65% oil dispersion, 460mg, 19.2mmol) was added at 0°C. The suspension was stirred at 0°C for 30min and at 60°C for 30min, and then CH3I (2.7g, 19.2mmol) was added. The resultant solution was continuously stirred at 60°C for 18h. After cooling to room temperature, the reaction solution was quenched with water. The resulting solid was filtrated and dried in vacuo to afford the title compound as a yellow solid (1.4g, 87%). 1H NMR (400MHz, DMSO-d6) δ 8.36-8.33 (m, 2H), 7.88-7.81 (m, 4H), 7.34 (ddd, J=7.9, 6.4, 1.4Hz, 2H), 3.95 (s, 3H). MS (ESI) m/z calcd for C14H11NO [M+ H]+, 210.1, found: 210.3.
84% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; 3 Preparation of 10-methylacridin-9(10H)-one (4) Take the 9(10H)-acridone (1.5g, 7.7mmol) prepared in Example 2 above, dissolve it in DMF, and protect it with N2.Add NaH (0.55g, 23mmol) at 0°C, stir for 30min and then add iodomethane (1.64g, 11.5mmol) with a syringe,Then it was transferred to room temperature and stirred for 4 hours. TLC detected that the reaction was complete. Intermediate 4 was obtained, 1.35 g of yellow solid, 84% yield
82.7% With sodium hydroxide In butanone at 55 - 60℃; for 3h;
81% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 18h; Acridinone A (10.0 g, 51.2 mmol) was dissolved in DMF (100 mL).Add NaH at 0 ° C (content: 60%, 5.12 g,128mmol),Stir at 60 ° C for 30 min,Add methyl iodide (8.0 mL, 128 mmol),Reaction at 60 ° C for 18 h,Cool to room temperature,Add water to quench the reaction,Filtering out solids,The filtrate was extracted with DCM (3×50 mL).Merge the DCM layer,Washed with saturated saline,Dry over anhydrous sodium sulfate,Concentrated under reduced pressure,The resulting residue is combined with the filter cake.Recrystallization of ethanol,Light yellow solid product,N-methyl-9-acridone B (8.7 g, 81% yield).
80% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
73% With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate for 0.0333333h; Irradiation; microwave;
71.1% With aluminum oxide; tetrabutylammomium bromide; potassium carbonate; sodium hydroxide at 65℃; for 0.25h; Microwave irradiation; 2.1.1 General procedure for the synthesis of N-alkyl-9(10H)-Acridone derivatives General procedure: The synthesis of the different N-alkyl acridone derivatives followed the synthetic procedure described by Wang et al. [38]. To a mixture of acridone (0.100g, 0.5mmol), K2CO3 (0.0071g, 0.18mmol), Al2O3 (0.0533g, 0.52mmol) NaOH (0.0071g, 0.18mmol) and TBAB (0.0017g, 0.005mmol) the proper alkyl halide, iodomethane, iodopentane or iodooctane, (2mL) was added on the 10mL microwave tube. The mixture was heated under microwave irradiation during 15minat 65°C with high speed stirring using a CEM (Discover SP) microwave oven. The reaction mixture was cooled at room temperature and the reaction product was purified by silica gel column chromatography using ethyl acetate and n-hexane (3:7) as eluent.
With potassium hydroxide 1.) EtOH, 20 min, reflux, 2.) DMF, 1 h, reflux; Yield given. Multistep reaction;
With sodium hydride 1.) DMF, 2.) DMF; Multistep reaction;
Stage #1: 10H-acridin-9-one With potassium hydroxide In ethanol at 125℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 165℃; for 0.666667h; ExamplePreparation of two-photon fluorescent probe 10-methyl-2-amino-acridone, as follows: Weigh 1.6277 g of potassium hydroxide, add 13 mL of absolute ethanol,Heating dissolves potassium hydroxide to form a mixture of potassium ethoxide. Add 0.4811 g acridone while hot,The temperature was raised to 125 ° C and ethanol was distilled off. Subsequently, 20 mL of N, N-dimethylformamide (DMF)The DMF was boiled at 165 ° C. Then slowly add 10 mL of methyl iodide, heat 40 min,While hot pour 50 mL ice water, after cooling yellow-green solid precipitation.Suction filtered, washed with 10 mL of ice water, dried at 70 , and further purified with absolute ethanol recrystallization.A yellow-green needle-like solid, ie 10-methyl-acridone. Precision weighed 0.2105 g10-Methyl-acridone In a three-necked flask, 6 mL of 99 wt% glacial acetic acid,And the temperature was raised to 40 ° C to dissolve the solid, followed by dropwise addition of 2 mL of concentrated nitric acid and 2 mL of 99 wt% glacial acetic acid,Stirring heated to 60 , the reaction 2 h. Pouring ice water while hot, golden yellow solid after cooling precipitation,Suction filtered, washed with 10 mL of ice water, the solid was placed in an oven, dried at 70 ° C to give a golden yellow solid, Ie 10-methyl-2-nitro-acridone.Precision Weigh 100 mg10-methyl-2-nitro-acridone in a round bottom flask,Add 5 mL ethanol and 2.5 mL Na2S solution (30 wt%), then add water to 50 mL,In the access to N2 conditions, heated to 130 ° C, the reaction 4 h. Pouring ice water while hot,After cooling there is yellowish solid precipitation. Suction filtered, washed with ice water, the solid placed in a vacuum oven,Dried at room temperature to give a khaki-colored solid, further purified by high performance liquid chromatography (HPLC)Obtained as a yellow needles solid 10-methyl-2-amino-acridone (MAA).
Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil
With potassium hydroxide In ethanol; N,N-dimethyl-formamide at 110 - 165℃; for 0.666667h;
With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 10h; Reflux;
In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; 1.1; 3.1 (1) In the reaction bottle, 100 mmol of raw material M is dissolved in DMF, under the protection of nitrogen, 100 mmol of methyl iodide is added, and the reaction is performed at room temperature for 3 hours; after the reaction is completed, water is added to the reaction solution.Stirred out solids, filtered, washed with water,Dry to get M1;

Reference: [1]Stopka, Tobias; Marzo, Leyre; Zurro, Mercedes; Janich, Simon; Würthwein, Ernst-Ulrich; Daniliuc, Constantin G.; Alemán, José; Mancheño, Olga García [Angewandte Chemie - International Edition, 2015, vol. 54, # 17, p. 5049 - 5053][Angew. Chem., 2015, vol. 127, # 17, p. 5137 - 5141,5]
[2]Wilkins, Lewis C.; Kim, Youngmin; Litle, Elishua D.; Gabbaï, François P. [Angewandte Chemie - International Edition, 2019, vol. 58, # 50, p. 18266 - 18270][Angew. Chem., 2019, vol. 131, p. 18434 - 18438,5]
[3]Iwama, Yusuke; Noro, Takahiro; Okano, Kentaro; Cho, Hidetsura; Tokuyama, Hidetoshi [Heterocycles, 2014, vol. 8, # 2, p. 1433 - 1444]
[4]Gosset; Xu; Maurel; Chamoreau; Nowak; Vives; Perruchot; Heitz; Jacquot De Rouville [New Journal of Chemistry, 2018, vol. 42, # 6, p. 4728 - 4734]
[5]Eberhard, Jens; Peuntinger, Katrin; Fröhlich, Roland; Guldi, Dirk M.; Mattay, Jochen [European Journal of Organic Chemistry, 2018, vol. 2018, # 20, p. 2682 - 2700]
[6]Location in patent: experimental part Maegawa, Yoshifumi; Mizoshita, Norihiro; Tani, Takao; Inagaki, Shinji [Journal of Materials Chemistry, 2010, vol. 20, # 21, p. 4399 - 4403]
[7]Sharma, Bharat K.; Shaikh, Azam M.; Agarwal, Neeraj; Kamble, Rajesh M. [RSC Advances, 2016, vol. 6, # 21, p. 17129 - 17137]
[8]Andronico, Luca A.; Quintavalla, Arianna; Lombardo, Marco; Mirasoli, Mara; Guardigli, Massimo; Trombini, Claudio; Roda, Aldo [Chemistry - A European Journal, 2016, vol. 22, # 50, p. 18156 - 18168]
[9]Song, Di; Zhang, Nan; Zhang, Panpan; Zhang, Na; Chen, Weijin; Zhang, Long; Guo, Ting; Gu, Xiaotong; Ma, Shutao [European Journal of Medicinal Chemistry, 2021, vol. 221]
[10]Current Patent Assignee: SHANDONG UNIVERSITY - CN113444080, 2021, A Location in patent: Paragraph 0075-0078
[11]Nishi, Hisao; Kohno, Hisao; Kano, Toshihiro [Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1897 - 1898]
[12]Current Patent Assignee: KUNMING SIAN BIOTECHNOLOGY - CN109928926, 2019, A Location in patent: Paragraph 0010
[13]Huang, Xiao-Ying; Ding, Rui; Mo, Zu-Yu; Xu, Yan-Li; Tang, Hai-Tao; Wang, Heng-Shan; Chen, Yan-Yan; Pan, Ying-Ming [Organic Letters, 2018, vol. 20, # 16, p. 4819 - 4823]
[14]Wang, Cunde; Hang, Tianlong; Zhang, Hui [Synthetic Communications, 2003, vol. 33, # 3, p. 451 - 456]
[15]Pereira, Ricardo C.; Pontinha, Ana Dora R.; Pineiro, Marta; Seixas de Melo, J. Sérgio [Dyes and Pigments, 2019, vol. 166, p. 203 - 210]
[16]Acheson, R. Morrin; Constable, Edwin C.; Wright, R. Gordon McR.; Taylor, Grahame M. [Journal of Chemical Research, Miniprint, 1983, # 1, p. 101 - 132]
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[18]Current Patent Assignee: FUJIAN MEDICAL UNIVERSITY - CN107311927, 2017, A Location in patent: Paragraph 0014
[19]Gini, Andrea; Uygur, Mustafa; Rigotti, Thomas; Alemán, José; García Mancheño, Olga [Chemistry - A European Journal, 2018, vol. 24, # 48, p. 12509 - 12514]
[20]Xia, Yaokun; He, Wenhui; Li, Juan; Zeng, Lupeng; Chen, Tingting; Liao, Yijuan; Sun, Weiming; Lan, Jianming; Zhuo, Shuangmu; Zhang, Jing; Yang, Huanghao; Chen, Jinghua [Analytical Chemistry, 2019, vol. 91, # 13, p. 8406 - 8414]
[21]Krokidis, Marios G.; Molphy, Zara; Efthimiadou, Eleni K.; Kokoli, Marianna; Argyri, Smaragda-Maria; Dousi, Irini; Masi, Annalisa; Papadopoulos, Kyriakos; Kellett, Andrew; Chatgilialoglu, Chryssostomos [Biomolecules, 2019, vol. 9, # 5]
[22]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN111233764, 2020, A Location in patent: Paragraph 0028-0032; 0048-0052
  • 14
  • [ 578-95-0 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide In butanone for 2h; Heating;
  • 15
  • [ 10072-05-6 ]
  • [ 88284-48-4 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
65% With cesium fluoride In tetrahydrofuran at 65℃; for 24h;
  • 16
  • [ 88284-48-4 ]
  • [ 85-91-6 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
72% With cesium fluoride In tetrahydrofuran at 65℃; for 24h;
  • 17
  • [ 719-54-0 ]
  • [ 2633-66-1 ]
  • 9-(2-mesityl)-10-methylacridinium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; 2-mesitylmagnesium bromide In tetrahydrofuran Stage #2: With sodium hydroxide In tetrahydrofuran
60% Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; 2-mesitylmagnesium bromide In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Stage #2: With perchloric acid In dichloromethane at 20℃; for 1h;
Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; 2-mesitylmagnesium bromide In dichloromethane Stage #2: With sodium hydroxide In dichloromethane Stage #3: With perchloric acid In dichloromethane
  • 18
  • [ 104-92-7 ]
  • [ 719-54-0 ]
  • 9-(4-methoxyphenyl)-10-methyl-9,10-dihydroacridin-9-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere;
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
  • 19
  • C20H17IN2 [ No CAS ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 24 h / 100 °C 2: aq.HCl / acetone
  • 20
  • [ 208664-53-3 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
82% With sodium sulfate; scandium tris(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 100℃; for 20h; Schlenk technique; Inert atmosphere; Green chemistry;
81% With [bis(acetoxy)iodo]benzene; dibenzoyl peroxide In N,N-dimethyl-formamide at 100℃; for 24h;
49% With [bis(acetoxy)iodo]benzene; dibenzoyl peroxide In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Sealed tube;
Multi-step reaction with 3 steps 1: MgSO4 / toluene / 100 °C 2: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 24 h / 100 °C 3: aq.HCl / acetone

  • 21
  • [ 719-54-0 ]
  • [ 674783-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CH2Cl2 2: aq. HClO4 / CH2Cl2
  • 22
  • [ 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
  • 23
  • [ 76041-86-6 ]
  • [ 719-54-0 ]
  • 24
  • [ 719-54-0 ]
  • [ 66762-83-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / diethyl ether; tetrahydrofuran / 0.5 h / Heating 2: oxygen / methylene blue / CH2Cl2 / 0.5 h / -78 °C
  • 25
  • [ 719-54-0 ]
  • [ 74975-63-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 35 percent / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature 2: oxygen / methylene blue / CH2Cl2 / 3 h / -78 °C
  • 26
  • [ 719-54-0 ]
  • [ 79-19-6 ]
  • [ 24283-96-3 ]
YieldReaction ConditionsOperation in experiment
With ammonia In methanol; trichlorophosphate 9 EXAMPLE 9 EXAMPLE 9 1.8 g of 10-methyl-9-acridanone are heated to boiling under reflux in 50 ml of phosphorus oxychloride for 1 hour, whereupon the solution is evaporated in vacuo. The residue is suspended in ether and filtered. The dried greenish powder, 9-chloro-10-methyl-acridinium dichlorophosphate, is dissolved in 100 ml of methanol, treated with 0.8 g of thiosemicarbazide and stirred at room temperature for 1 hour. The precipitated product is filtered, washed with ethanol and ether and heated to boiling for 10 minutes with 50 ml of concentrated ammonia. The mixture is filtered while hot and washed successively with water, ethanol and ether. There is obtained 10-methyl-9-acridanone thiosemicarbazone of melting point 196°-198° (decomposition).
  • 27
  • [ 719-54-0 ]
  • [ 75586-67-3 ]
YieldReaction ConditionsOperation in experiment
87% With thionyl chloride for 2h; Inert atmosphere; Reflux; 4 Preparation of 10-methyl-9-chloroacridinium chloride (5) Take the 10-methylacridine-9(10H)-one (0.2g, 0.96mmol) prepared in Example 3 above, dissolve it in thionyl chloride, protect it with N2, and stir for 2h under reflux.TLC detects that the reaction is complete. After the solvent is removed by rotary evaporation, Intermediate 5 is obtained, 0.22 g of yellow solid, and the yield is 87%
With thionyl chloride at 20℃; for 1h;
With 1,2,4-Triazole; triethylamine; trichlorophosphate In dichloromethane; acetonitrile at 0℃; for 48h; Cooling with ice; Reflux;
With thionyl chloride In N,N-dimethyl-formamide Reflux;
With thionyl chloride for 2h; Inert atmosphere; Reflux; 5.2.4. 9-Chloro-10-methylacridin-10-ium chloride (5) Intermediate 4 (150mg, 0.57mmol) was dissolved in SOCl2 (4mL) and the mixture was refluxed under nitrogen atmosphere for 2h. After the completion of the reaction, intermediate 5 was obtained as a light yellow solid after concentration under reduced pressure at 50°C to remove the excess of SOCl2. This intermediate could be used in the next step without purification.

  • 28
  • [ 719-54-0 ]
  • [ 1083163-48-7 ]
YieldReaction ConditionsOperation in experiment
30% With chlorosulfonic acid In paraffin oil at 60℃; for 24h; Inert atmosphere; 2.1.2 General procedure for the synthesis of N-alkyl-9(10H)-acridone-2,7-disulfonyl dichloride General procedure: To the N-alkyl-9(10H)acridone (0.100g) chlorosulfonic acid (2.5mL, 0.38mmol) was added and placed under inert atmosphere in a paraffine bath at 60°C during 24hat vigorous stirring. The solution is left to cool in ice and a saturated solution of NaHCO3 (25mL) was added. Then 20mL of chloroform were added and the organic layer extracted. The organic layer was washed three times with water, dried with sodium sulfate anhydrous and filtrated. The evaporation of chloroform under vacuum yield the N-alkyl-9(10H)-acridone-2,7-disulfonyl dichloride as yellow solids.
With chlorosulfonic acid for 5h; Reflux; 2 EXAMPLE 2; 10-methyl-9-oxo-9,10-dihydroacridine-2,7-disulfonyl dichloride; A mixture of 10-methylacridin-9(10H)-one (4.2 g, 20 mmole) and chlorosulfonic acid (100 ml_, 1.5 mole) was heated at reflux for 5 hours.Reaction mixture was then condensed, cooled down to room temperature and poured carefully on 500 g of ice. The yellow precipitate of product was collected by filtration, washed with water and dried to provide 8.1 g of the title compound. This material was used for next step without purification.
8.1 g With chlorosulfonic acid for 5h; Reflux; 7 10-methyl-9-oxo-9,10-dihydroacridine-2,7-disulfonyl dichloride A mixture of 10-methylacridin-9(10H)-one (4.2 g, 20 mmole) and chlorosulfonic acid (100 mL, 1.5 mole) was heated at reflux for 5 hours. Reaction mixture was then condensed, cooled down to room temperature and poured carefully on 500 g of ice. The yellow precipitate of product was collected by filtration, washed with water and dried to provide 8.1 g of the title compound. This material was used for next step without purification.
With chlorosulfonic acid In chloroform for 6h; Cooling with ice; Reflux; 22 Example 22 Example 22 Synthesis of 9,10-dimethyl-2,7-disulfoacridin-10-ium 10-methylacridin-9-one (1.0 g) was dispersed in 10 mL of anhydrous chloroform in a 100 mL round bottom flask and cooled in an ice bath. Chloropsulfonic acid (1.9 mL) was added dropwise. After the addition, the flask was fitted with a condenser and heated to reflux for 6 h. The reaction was quenched by addition of 25 g of crushed ice and solid product isolated by filtration, washed with three portions of ice water and dried in vacuum to give 10-methylacridin-9-one-2,7-disulfonyl chloride.

  • 29
  • [ 109392-90-7 ]
  • [ 719-54-0 ]
  • [ 108-95-2 ]
  • 30
  • [ 719-54-0 ]
  • [ 17014-39-0 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 80℃;
90% With bromine; acetic acid for 20h; Reflux;
80% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 90℃; for 24h; Inert atmosphere; Schlenk technique;
  • 31
  • [ 455300-83-1 ]
  • [ 88284-48-4 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: o-fluorobenzaldehyde N,N-dimethylhydrazone; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With cesium fluoride In acetonitrile at 65℃; for 10h; Stage #2: With hydrogenchloride; water; sodium methylate In acetonitrile at 65 - 100℃; for 4h;
  • 32
  • [ 5051-47-8 ]
  • [ 88284-48-4 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 2-chlorobenzaldehyde dimethylhydrazone; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With cesium fluoride In acetonitrile at 65℃; for 10h; Stage #2: With hydrogenchloride In acetonitrile at 65℃; for 4h; Stage #3: With water; sodium methylate In acetonitrile at 100℃; for 2h;
  • 33
  • [ 88284-48-4 ]
  • [ 148492-28-8 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; 2-Bromobenzaldehyde N,N-dimethylhydrazone With cesium fluoride In acetonitrile at 65℃; for 10h; Stage #2: With hydrogenchloride In acetonitrile at 65 - 100℃; for 4h; Stage #3: With water In acetonitrile at 100℃; for 2h;
  • 34
  • [ 719-54-0 ]
  • [ 1774-34-1 ]
  • [ 29420-49-3 ]
  • [ 1306757-05-0 ]
YieldReaction ConditionsOperation in experiment
Example 1-1Synthesis of Compound No. 1A 200 ml four-necked flask was charged with 65.44 g (0.6810 mol) of methanesulfonic acid and 6.44 g (0.0454 mol) of phosphorous pentoxide. After purging with nitrogen, the contents were heated to 100 C. to dissolve. After cooling, 9.50 g (0.0454 mol) of N-methylacridone and 10.63 g (0.0454 mol) of bis(hydroxyphenyl) sulfoxide were added thereto and caused to react at 50 C. for 4 hours. The reaction mixture was poured into a mixture of 180 g of ice water, 190 g of methanol, and 110 g of isopropyl ether in a 1 L beaker, stirred for 1 hour, and left to stand. The upper layer was discarded. To the lower layer were added 370 g of methylene chloride and 23.10 g (0.0683 mol) of potassium nonafluorobutanesulfonate, followed by stirring for 1.5 hours. The methylene chloride layer was washed with three 160 g portions of water and concentrated under reduced pressure to give 23.29 g of compound No. 1 of the invention (composed of cation No. 1 and a nonafluorobutanesulfonate anion) (yield: 70.6%; HPLC purity: 94.6%).
  • 35
  • [ 719-54-0 ]
  • [ 395-25-5 ]
  • C26H18F2NOS(1+)*F6Sb(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; bis(4-fluorophenyl)sulfoxide With methanesulfonic acid; phosphorus pentoxide at 50℃; for 4h; Inert atmosphere; Stage #2: With potassium hexafluoroantimonate In dichloromethane for 1h; 1-6.1 Example 1-6Synthesis of Compound No. 6Step 1-Synthesis of Intermediate No. 6A 50 ml four-necked flask was charged with 18.74 g (0.195 mol) of methanesulfonic acid and 1.845 g (0.013 mol) of phosphorous pentoxide. After purging with nitrogen, the contents were heated to 100° C. to dissolve. After cooling, 2.72 g (0.013 mol) of N-methylacridone and 3.10 g (0.013 mol) of bis(fluorophenyl) sulfoxide were added thereto and caused to react at 50° C. for 4 hours. The reaction mixture was poured into a mixture of 30 ml of ice water, 25 ml of methanol, and 25 ml of isopropyl ether in a 500 ml beaker, stirred for 1 hour, and allowed to stand. The upper layer was removed. To the lower layer were added 140 ml of methylene chloride and 4.64 g (0.0169 mol) of KSbF6, followed by stirring for 1 hour. The methylene chloride layer was washed with three 70 g portions of water, and the solvent was removed by evaporation to afford 8.27 g of intermediate No. 6.
  • 36
  • [ 719-54-0 ]
  • [ 36519-61-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 24 h / 20 °C 2: perchloric acid / water / 100 °C
  • 37
  • [ 19836-78-3 ]
  • [ 88284-48-4 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
33% In acetonitrile at 20℃; for 24h;
  • 38
  • [ 4295-36-7 ]
  • [ 719-54-0 ]
  • 39
  • [ 7601-90-3 ]
  • [ 719-54-0 ]
  • [ 576-83-0 ]
  • [ 674783-97-2 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2,4,6-trimethylphenyl bromide With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.5h; Cooling with acetone-dry ice; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In diethyl ether; pentane at -78 - 25℃; for 72h; Cooling with acetone-dry ice; Stage #3: perchloric acid In ethyl acetate
  • 40
  • [ 1859-76-3 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
97% With [2,2]bipyridinyl; copper(l) iodide; oxygen In N,N-dimethyl acetamide at 140℃; for 12h; Sealed tube;
84% With copper(I) thiophene-2-carboxylate; oxygen; triphenylphosphine; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 23h;
78% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 12h;
  • 41
  • [ 719-54-0 ]
  • [ 576-83-0 ]
  • 9-(2-mesityl)-10-methylacridinium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2,4,6-trimethylphenyl bromide With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.55h; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In diethyl ether; pentane at -78 - 25℃; for 73h; Stage #3: With perchloric acid In ethyl acetate
  • 42
  • [ 62-53-3 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: copper diacetate; sodium acetate / water / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / Cooling with ice 2.2: 2 h / 80 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 5.1: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / Schlenk technique; Inert atmosphere; Green chemistry
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; copper(I) oxide / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 5.1: [bis(acetoxy)iodo]benzene; dibenzoyl peroxide / N,N-dimethyl-formamide / 24 h / 100 °C
Multi-step reaction with 3 steps 1.1: copper; potassium carbonate / ethanol / 12 h / Reflux 2.1: sulfuric acid / 6 h / 100 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 60 °C 3.2: 18 h / 60 °C
Multi-step reaction with 5 steps 1.1: copper(I) oxide; 4-methyl-morpholine / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.1: polyphosphoric acid / 3 h / 100 °C 3.1: borane-THF / tetrahydrofuran / 80 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C / Schlenk technique; Inert atmosphere 4.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 5.1: iron(II) chloride; di-tert-butyl peroxide; ethyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate / dichloromethane / 48 h / 20 °C / 760.05 Torr
Multi-step reaction with 3 steps 1.1: potassium carbonate; copper / ethanol / 12 h / Reflux 2.1: sulfuric acid / 6 h / 100 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 3.2: 4 h / 20 °C / Inert atmosphere

  • 43
  • [ 719-54-0 ]
  • [ 63463-36-5 ]
  • [ 51685-15-5 ]
YieldReaction ConditionsOperation in experiment
76% In tetrahydrofuran at 0℃;
  • 44
  • [ 169170-03-0 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
95% With boron trifluoride diethyl etherate In neat (no solvent) at 150℃; for 0.0166667h; Microwave irradiation;
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 3: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / Schlenk technique; Inert atmosphere; Green chemistry
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 3: [bis(acetoxy)iodo]benzene; dibenzoyl peroxide / N,N-dimethyl-formamide / 24 h / 100 °C
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 30 °C / Inert atmosphere; Sealed tube 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C / Inert atmosphere; Sealed tube 3: [bis(acetoxy)iodo]benzene; dibenzoyl peroxide / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere; Sealed tube

  • 46
  • [ 91-40-7 ]
  • [ 719-54-0 ]
  • [ 30713-65-6 ]
  • 47
  • [ 38609-97-1 ]
  • [ 719-54-0 ]
  • C15H10NO6S(1-) [ No CAS ]
  • 48
  • [ 719-54-0 ]
  • 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one [ No CAS ]
  • 10-methyl-1-((triisopropylsilyl)ethynyl)acridin-9(10H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 12h; regioselective reaction;
  • 49
  • [ 55-21-0 ]
  • 10-methylacridin-10-ium methyl sulfate [ No CAS ]
  • [ 719-54-0 ]
  • N-(10-methyl-10H-acridin-9-ylidene)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 79% 2: 6% Stage #1: benzamide With sodium hydride In dimethyl sulfoxide; paraffin oil for 0.5h; Stage #2: 10-methylacridin-10-ium methyl sulfate With potassium hexacyanoferrate(III) In dimethyl sulfoxide; paraffin oil for 3h; Benzamidation of N-methylacridinium methyl sulfate(13). The reaction was performed in a vessel protectedfrom air moisture. Sodium hydride (60% suspension in oil,120 mg, 3 mmol) was added with stirring to a solution ofbenzamide (363 mg, 3 mmol) in anhydrous DMSO (4 ml).After the evolution of hydrogen ceased (~0.5 h), N-methylacridiniummethyl sulfate (13) (152.5 mg, 0.5 mmol) andK3Fe(CN)6 (1 g, 3 mmol) were added, and the reactionmixture was vigorously stirred for 3 h. The mixture wasthen poured on crushed ice (~50 g), allowed to warm toroom temperature, and acidified with dilute HCl solution topH ~7. The precipitate was filtered off, washed with water,and dried. The obtained mxture was separated by dry silicagel flash chromatography,26 eluting the first fraction withbenzene and the second fraction with ethyl acetate. Thefirst colorless fraction after evaporation of solvent gave83 mg (79%) of 10-methyl-10H-acridin-9-one (15).Yellow crystals, mp 202-203° (benzene) (mp 203°(benzene)27). The second, pale-yellow fraction contained19 mg (6%) of N-(10-methyl-10H-acridin-9-ylidene)-benzamide (14). Yellow crystals, mp 187-188° (EtOAc).1H NMR spectrum (DMSO-d6), δ, ppm (J, Hz): 3.92 (3H,s, CH3); 7.25 (2H, dd, J = 7.8, J = 8.2, H-2,7); 7.49 (2H, br.t, J = 7.5, H-3',5' Ph); 7.58 (1H, br. t, J = 7.3, H-4' Ph);7.76 (2H, dd, J = 7.8, J = 8.2, H-3,6); 7.81 (2H, br. d,J = 8.2, H-4,5); 7.96 (2H, d, J = 7.8, H-2',6' Ph); 8.04 (2H,dd, J = 8.2, J = 1.2, H-1,8). 13C NMR spectrum (DMSO-d6),δ, ppm: 34.4 (CH3); 116.2 (C-4,5); 117.9 (C-8a,9a); 121.6(C-2,7); 127.1 (C-1,8); 128.6 (C-2',6'); 128.7 (C-3',5'); 132.3 (C-4'); 133.4 (C-3,6); 134.5 (C-1'); 141.4 (C-4a,10a);152.7 (C-9); 176.0 (C=O). Found, m/z: 313.1349 [+H]+.C21H17N2O. Calculated, m/z: 313.1335.
  • 50
  • [ 700-58-3 ]
  • [ 719-54-0 ]
  • 9-((1r,3r,5r,7r)-adamantan-2-ylidene)-10-methyl-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane at 0℃; for 1.5h; Inert atmosphere; Reflux;
  • 51
  • [ 719-54-0 ]
  • [ 100-58-3 ]
  • [ 36519-61-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; phenylmagnesium bromide In dichloromethane Stage #2: With sodium hydroxide In dichloromethane Stage #3: With perchloric acid In dichloromethane
  • 52
  • [ 719-54-0 ]
  • [ 30713-65-6 ]
YieldReaction ConditionsOperation in experiment
68% With methanol; sodium tetrahydroborate 9 The first step will be 10g10-methyl-9 (10H) -acridone was added to 100 ml of methanol, and at room temperature, 20 gSodium borohydride was added to the solution. Reaction process has hydrogen evolution, through the TLC monitoring reaction process. To 10-methyl-9 (10H) -After the acridone is completely reacted, the solvent methanol is distilled off and then dissolved in dichloromethane and the organic phase is washed with deionized water Times, the pH of the aqueous phase is reduced to 7.0. The organic phase was collected and concentrated, and the product was separated after crystallization of the hydroxylated product. Reaction and posterior The process should be noted in an inert atmosphere to prevent oxidation of the hydroxylated product. The reaction yield was 68%.
  • 53
  • [ 36259-22-0 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
81% With 1,10-Phenanthroline; oxygen; copper diacetate; palladium diacetate; silver carbonate In N,N-dimethyl-formamide at 120℃; for 12h; 2 Example 2 The substrate was 2- (2- (methylamino) benzoyl) benzoic acid (127.5 mg, 0.5 mmol), anhydrous 1,10-phenanthroline(9 mg, 0.05 mmol)Copper acetate (11.4 mg, 0.05 mmol), palladium acetate (6 mg, 0.025 mmol)Silver carbonate (13.8 mg, 0.05 mmol),Anhydrous DMF 1.3 mL In a 10 ml reactor,The mixture was stirred at 120 ° C for 12 h,After completion of the reaction, an appropriate amount of water (20 ml x 3) and ethyl acetate (20 ml)The organic phase was washed with saturated brine (20 ml)Dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography on silica gel,With petroleum ether / ethyl acetate volume ratio of 1 to 3: 1 mixture for washingThe eluate was collected and the solvent was evaporated and dried to give the product 10-methyl-9 (10H) -acridineKetone 84 mg, yield 81%, product as a yellow solid
  • 54
  • [ 719-54-0 ]
  • [ 121-69-7 ]
  • 9-(4-(dimethylamino)phenyl)-10-methylacridin-10-ium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 10-methyl-9, 10-dihydro-9-acridinone; <i>N</i>,<i>N</i>-dimethyl-aniline With trichlorophosphate at 90℃; for 2h; Inert atmosphere; Stage #2: With perchloric acid In acetonitrile Inert atmosphere;
  • 55
  • [ 719-54-0 ]
  • [ 58658-02-9 ]
YieldReaction ConditionsOperation in experiment
91% With nitric acid; acetic acid at 50℃; for 2h;
With nitric acid; acetic acid at 40 - 60℃; for 2h; ExamplePreparation of two-photon fluorescent probe 10-methyl-2-amino-acridone, as follows: Weigh 1.6277 g of potassium hydroxide, add 13 mL of absolute ethanol,Heating dissolves potassium hydroxide to form a mixture of potassium ethoxide. Add 0.4811 g acridone while hot,The temperature was raised to 125 ° C and ethanol was distilled off. Subsequently, 20 mL of N, N-dimethylformamide (DMF)The DMF was boiled at 165 ° C. Then slowly add 10 mL of methyl iodide, heat 40 min,While hot pour 50 mL ice water, after cooling yellow-green solid precipitation.Suction filtered, washed with 10 mL of ice water, dried at 70 , and further purified with absolute ethanol recrystallization.A yellow-green needle-like solid, ie 10-methyl-acridone. Precision weighed 0.2105 g10-Methyl-acridone In a three-necked flask, 6 mL of 99 wt% glacial acetic acid,And the temperature was raised to 40 ° C to dissolve the solid, followed by dropwise addition of 2 mL of concentrated nitric acid and 2 mL of 99 wt% glacial acetic acid,Stirring heated to 60 , the reaction 2 h. Pouring ice water while hot, golden yellow solid after cooling precipitation,Suction filtered, washed with 10 mL of ice water, the solid was placed in an oven, dried at 70 ° C to give a golden yellow solid, Ie 10-methyl-2-nitro-acridone.Precision Weigh 100 mg10-methyl-2-nitro-acridone in a round bottom flask,Add 5 mL ethanol and 2.5 mL Na2S solution (30 wt%), then add water to 50 mL,In the access to N2 conditions, heated to 130 ° C, the reaction 4 h. Pouring ice water while hot,After cooling there is yellowish solid precipitation. Suction filtered, washed with ice water, the solid placed in a vacuum oven,Dried at room temperature to give a khaki-colored solid, further purified by high performance liquid chromatography (HPLC)Obtained as a yellow needles solid 10-methyl-2-amino-acridone (MAA).
With nitric acid; acetic acid at 58 - 62℃; for 2h;
  • 56
  • [ 719-54-0 ]
  • [ 95962-62-2 ]
  • C46H34N2(2+)*2F6P(1-)*2C2H3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 3,3''-dibromo-1,1':3',1''-terphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Schlenk technique; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In tetrahydrofuran; hexane at -78 - 20℃; Schlenk technique; Further stages;
  • 57
  • C22H20N2O2S [ No CAS ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In methanol at 20℃; II. Synthesis of Acridones from Triazoles A. Typical Procedure Triazole 7d (161 mg, 0.4 mmol) and Rh2(OAc)4 (3 mg, 2 mol%) were added to a 25 mL round bottom flask equipped with a stirrer bar, then 4 mL of toluene was added to the flask. The reaction mixture was stirred for 2 h at 80 oC under nitrogen. Then it was cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with methanol (4 mL), then K2CO3 (220 mg, 1.6 mmol) was added to the mixture. The new reaction mixture was stirred at room temperature overnight. Then the mixture was filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography on silica gel using PE/EA as the eluent to give 11d: 48 mg, 57%, light yellow solid, mp = 202-204 °C. 1H NMR (400 MHz, CDCl3) δ 8.54 (dd, J = 8.0, 1.6 Hz, 2H), 7.71 - 7.67 (m, 2H), 7.48 (d, J = 8.7 Hz, 2H), 7.26 (t, J = 7.5 Hz, 2H), 3.85 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 178.0, 142.5, 133.8, 127.7, 122.4, 121.3, 114.8, 33.7. The 1H NMR matches the reported literature.5
  • 58
  • [ 201230-82-2 ]
  • [ 1290129-46-2 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: carbon monoxide With cesium pivalate; tricyclohexylphosphine tetrafluoroborate; palladium dichloride In N,N-dimethyl-formamide at 120℃; for 0.5h; Schlenk technique; Green chemistry; Stage #2: N-2-bromophenyl-N-phenylaminomethane In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Green chemistry; 1 Example 1 0.01 mmol of palladium chloride, 0.02 mmol of tricyclohexylphosphine tetrafluoroborate and 0.6 mmol of cesium pivalate were added to the dried Schlenk tube.The gas atmosphere in the Schlenk tube is replaced by air to carbon monoxide, and the system is replaced three times in a standard atmospheric carbon monoxide atmosphere to ensure a pure carbon monoxide atmosphere; Under an atmosphere of carbon monoxide gas, 2 mL of anhydrous N,N-dimethylformamide was added, heated to 120 ° C, and stirred for 30 minutes;0.2 mmol of N-methyl-2-bromodiphenylamine was added, and the reaction was carried out at 120 ° C for 12 hours, and cooled to room temperature;The reaction was quenched by adding 4 mL of a saturated ammonium chloride solution, and 8 mL of water was added, followed by extraction with ethyl acetate.Separation and purification by column chromatography gave an acridone derivative, and the separation and collection rate of this example reached 78%.
78% With N,N-dimethyl-formamide; cesium pivalate; tricyclohexylphosphine tetrafluoroborate; palladium dichloride at 120℃; for 12h; Schlenk technique; Palladium catalyzed cyclization for synthesis of acridone. General procedure: To an oven dried Schlenk tube containing PdCl2 (1.8 mg, 5 mol %), PCy3HBF4 (7.4 mg, 10 mol %), PivOCs (140 mg, 0.6 mmol), a balloon filled with CO was connected to the Schlenk tube via the side tube and purged 3 times. DMF (2 mL) was added to the tube under CO atmosphere. The mixture was stirred at 120 for 30 min before the substrate of 1a was added to the Schlenk tube. The mixture was continued to stir at 120 for 12 h and then cooled to room temperature. After quenched by saturated ammonium chloride solution, the mixture was extracted with ethyl acetate three times. The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The desired products of acridone (2a) were obtained in 78% yields after purification by flash chromatography on silica gel with petroleum ether/ethyl acetate. acridone (2a) 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J = 8.0 Hz, 2H), 7.69 (t, J = 7.9 Hz, 2H), 7.48 (d, J = 8.7 Hz, 2H), 7.27 (t, J = 7.5 Hz, 2H), 3.85 (s, 3H) ppm; 13C NMR (101 MHz, CDCl3) δ 178.0, 142.4, 133.7, 127.6, 122.3, 121.1, 114.7, 33.5 ppm.
  • 59
  • (2-bromophenyl)(2-(methylamino)phenyl)methanone [ No CAS ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
95% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 0.0833333h;
  • 60
  • [ 26767-16-8 ]
  • [ 719-54-0 ]
  • 61
  • [ 719-54-0 ]
  • [ 72434-06-1 ]
  • C21H16ClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: ((4-chlorophenyl)thio)methyltriphenylphosphonium chloride With n-butyllithium In tetrahydrofuran at -50℃; for 0.5h; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In tetrahydrofuran at -50 - 20℃; for 2h; (4-Chlorophenyl)thio)methyltriphenylphosphonium chloride (28.4 g, in a 250 mL single-necked flask,62.4 mmol) and anhydrous tetrahydrofuran (100 mL),Cool down to -50 ° C,Adding a concentration of 2.2M n-butyl lithium tetrahydrofuranThe solution (34 mL, 74.9 mmol) was added dropwise and stirred at -50 ° C for 30 min.N-methyl-9-acridone B (8.7 g, 41.6 mmol) was added in portions and the temperature was gradually increased after completion of the addition.And reacted at room temperature for 2 h,Add water to quench the reaction,Ethyl acetate extraction (3X80mL),Combine the organic phase,Dry over anhydrous sodium sulfate,Concentrate the solvent under reduced pressure.The residue was recrystallized from tert-butyl methyl ether.Made a pale yellow oily liquid,For intermediate C (12.4 g, 85% yield).
  • 62
  • [ 719-54-0 ]
  • 9,9-dichloro-10-methyl-9,10-dihydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride at 60℃; for 2h; 6 9,9-Dichloro-lO-methyl-9,lO-dihydroacridine (5): Compound 4 (10 g, 4.85 mmol, 1.0 equiv) in thionyl chloride (200 mL, 2.75 mol, 55 equiv) was stirred at 60 °C for 2 hours, at which point 1H-NMR indicated the reaction was complete. The thionyl chloride was removed under reduced pressure. The residue was azeotroped with toluene (2 x 20 mL) to give crude compound 5 as a yellow solid (12.5 g), which was used subsequently.
  • 63
  • sodium hexafluoroantimonate [ No CAS ]
  • [ 719-54-0 ]
  • [ 501-65-5 ]
  • 2,3-diphenyl-7-methyl-7H-pyrano[4,3,2-kl]acridin-1-ium hexafluoroantimonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In tetrahydrofuran at 80℃; for 10h;
69% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In tetrahydrofuran at 80℃; for 10h; 3 Synthesis of 2,3-diphenyl-7-methyl-7H-pyrano[4,3,2-kl]acridin-1-ium hexafluoroantimonate (III-a) (1) Combine N-methylacridone (41.8mg, 0.20mmol), diphenylacetylene (71.2mg, 0.40mmol), [Cp*RhCl2]2 (3.1mg, 5μmol, 2.5mol%), AgOAc (66.8 mg, 0.40mmol), AgSbF6 (13.7mg, 40μmol, 20mol%), NaSbF6 (51.7mg, 0.20mmol) and tetrahydrofuran (1.0mL) were added to the reaction tube and stirred uniformly, heated to 80°C and reacted for 10 hours;(2) After the reaction is completed, cool the reaction tube to room temperature, add 10 mL of dichloromethane to dilute the reaction system,Then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrate,The solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (dichloromethane/ethyl acetate=20:1, v/v). After vacuum drying, the target product 2,3-diphenyl- was obtained as a pale yellow solid. 7-methyl-7H-pyrano[4,3,2-kl]acridin-1-ium hexafluoroantimonate (III-a) 85.7 mg, yield 69%.
  • 64
  • [ 129112-26-1 ]
  • [ 85-91-6 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
45% With triethylsilane; cesium fluoride In tetrahydrofuran at 70℃; for 24h; Inert atmosphere;
  • 65
  • [ 719-54-0 ]
  • [ 6290-49-9 ]
  • methyl 2-methoxy-2-(10-methylacridin-9(10H)-ylidene)acetate [ No CAS ]
  • methyl 2-(10-methylacridin-9(10H)-ylidene)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 9% Stage #1: 10-methyl-9, 10-dihydro-9-acridinone With titanium tetrachloride In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: methyl methoxyacetate With triethylamine In dichloromethane for 24h; Inert atmosphere; Reflux; General procedure of olefination: General procedure: In a doule-heated three-necked flask with a reflux condenser and septum, TiCL4 (1.25 eq.) was slowly added under argon atmosphere to the ketone compound (1.00 eq.) dissolved in dry CH2Cl2 (12 mL per mmol ketone compound). The mixture was stirred for 15 min at room temperature. Methyl 2-methoxy acetate (2.00 eq.) and triethylamine or DIPEA (13.5 eq) were added consecutively to the reaction mixture which was subsequently heated under reflux for 24h. An aqueous solution of HCl (1M) was added to the cooled-down reaction mixture until a clear solution emerged and extracted three times with CH2Cl2. The combined organic phase were washed with brine, dried over MgSO4 or NaSO4, and filtered, and the solvent was removed in vacuo. The residue was purified via column chromatography on SiO2.
  • 66
  • methyl 2-(10-methylacridin-9(10H)-ylidene)acetate [ No CAS ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
With oxygen In chloroform-d1 at 25℃; Irradiation; General procedure for photooxygenation: General procedure: In NMR tube, the olefin (20 mg) was dissolved in CDCLNo. (1 mL). An amount of 0.1 mg of TPP (c= 1.63x 10-4 mol/L)was added, and the solution was saturated with oxygen over an inlet under light irradiation with two halogen lamps (150W each) at 25 C. Thereaction progressed via 1H-NMR after certain periods of time. After the reaction was completed, product/ products were not worked up or purified.
  • 67
  • [ 92-81-9 ]
  • [ 719-54-0 ]
  • 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: copper(I) bromide; tert.-butylhydroperoxide / dichloromethane / 48 h / 20 °C / 760.05 Torr
  • 68
  • [ 719-54-0 ]
  • [ 85191-66-8 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 10-methyl-9-acridanone With sodium tetrahydridoborate In methanol Inert atmosphere; Schlenk technique; Stage #2: With hydrogen hexafluorophosphate (V); acetic anhydride In water monomer at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique;
  • 69
  • [ 719-54-0 ]
  • [ 2315-97-1 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 10-methyl-9-acridanone With hydrogenchloride; zinc at 78℃; for 0.5h; Stage #2: With HNO3 In lithium hydroxide monohydrate at 90℃; for 3h; 1-6; 1 In the 500mL reaction bottle, N-methylacridone (10g, 48mmol), ethanol (200mL) and zinc powder (3g, 46mmol, average particle size of 200μm), stirred to heat up to reflux, and then added 11.5g of concentrated hydrochloric acid with a mass fraction of 30%, reflux reaction at 78 °C for 0.5h, sampling pH >3, TLC central control, there is raw material N-methylacidone remaining, and then add zinc powder (1.5g, 23mmol, The average particle size is 200 μm), continue to reflux reaction at 78 °C 0.5 h, sampling pH3, TLC central control, the content of raw material N-methylacridone is significantly less, and then add zinc powder (1g, 15 mmol, average particle size of 200 μm), continue to reflux reaction at 78 °C 0.5h, sampling detection, the reaction is basically complete, continue to insulation reaction at 78 °C for 0.5h, cool down to 20 °C, filter, that is, obtained. The molar amount of HCl used in the present embodiment of concentrated hydrochloric acid is 0.0945mol, the ratio of HCl to the molar amount of N- methylacridone is 1.97:1. Example 6 The preparation method of the acridine salt compound of the present embodiment, comprises the following steps: The filter cake obtained by filtration of Example 3 was added to the 2L reaction flask, Then add 710mL of water to the reaction flask, Then 420g of nitric acid solution with a mass fraction of 65% was added dropwise, At this time, the pH of the reaction system was less than 1. After the dropwise addition was completed, The reaction system was heated to 90 °C, and the reaction was refluxed for 3 h. Sampling and measuring pH=34, then adding 120 g of nitric acid solution with a mass fraction of 65% to the reaction system, sampling and measuring pH=23, The reaction system was kept at 90 °C for 1 h. Sampling and measuring pH=34, a reddish-brown solution is obtained, Then the reddish-brown solution with a temperature of 90 ° C is subjected to the first filtration treatment, The filtrate obtained by the first filtration treatment was cooled to 20°C for 1 hour of crystallization, Then perform the second filtering process, The filter cake obtained by the second filtration treatment was washed twice with 500 mL of chloroform, Finally, the washed filter cake was dried at 60°C, The obtained product was 777.8 g with a purity of 99.3% and a yield of 89%. The organic filtrate in the preparation process is recycled, The aqueous filtrate is treated as acidic wastewater, The remaining waste is treated as organic waste. The molar amount of HNO in the nitric acid solution used in the present embodiment is 5.57 mol, The molar ratio of HNO3 to N-methylacridone used in Example 3 was 3.28:1.
  • 70
  • [ 2915392-54-8 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide In dimethyl sulfoxide 2.5. Chemiluminescence spectra measurement of compounds 9- 12 General procedure: To 0.5 mL of a 0.1 mM solution of compounds 9- 12 in dimethyl sulfoxide in a quartz cell (10 × 10 × 50 mm) was added 1 mL of a buffer solution (pH 7- 10). The mixture was allowed to stand for 20 s, and the CL reaction was initiated by adding 1 mL of a 100 mM aqueous hydrogen peroxide solution. After 60 s, the mixture was placed in a fluorimeter (FP 6500), and the CL emission spectra were measured.
  • 71
  • [ 2915392-56-0 ]
  • [ 719-54-0 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide In dimethyl sulfoxide 2.5. Chemiluminescence spectra measurement of compounds 9- 12 General procedure: To 0.5 mL of a 0.1 mM solution of compounds 9- 12 in dimethyl sulfoxide in a quartz cell (10 × 10 × 50 mm) was added 1 mL of a buffer solution (pH 7- 10). The mixture was allowed to stand for 20 s, and the CL reaction was initiated by adding 1 mL of a 100 mM aqueous hydrogen peroxide solution. After 60 s, the mixture was placed in a fluorimeter (FP 6500), and the CL emission spectra were measured.
  • 72
  • [ 108-86-1 ]
  • [ 719-54-0 ]
  • [ 6321-72-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Heating; Stage #2: 10-methyl-9, 10-dihydro-9-acridinone In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique; 9-phenyl-10-methylacridinium triflate (1a) Phenylmagnesium bromide (Grignard) reagents were made on demand for specific redox mediator synthesis. In a dry flask attached to a Schlenk line, with a dry stir bar, 1 equiv. of dried Mg powder and a few small crystals of I2 were added and the headspace was purged with Ar gas. One equivalent of bromobenzene dissolved in dry tetrahydrofuran (THF; 20 ml) was added to the Mg powder. The solution was briefly heated to begin the reaction and then placed in an ambient-temperature water bath. The reaction mixture was then stirred for 60 min. Once completed, the crude Grignard reagent was used without isolation for subsequent steps. 1a was made by a modified procedure taken from the literature36. First the acridinol analogue (9-phenyl-10-methylacridin-9-ol) was made by first dissolving 10-methylacridinone (0.50 g, 2.39 mmol, 1 equiv.) in dry THF (50 ml), then the 10-methylacridinone was added dropwise to an Ar-purged, phenylmagnesium bromide-containing (2.2 equiv.) Schlenk flask over a 20-min period. The flask was chilled to 0 °C in an ice bath during 10-methylacridinone addition, then allowed to warm to room temperature and stirred for 24 h. The reaction was quenched with aqueous NH4Cl (10 ml) and diluted with ethyl acetate (EtOAc) and H2O. The aqueous layer was extracted with EtOAc three times. The resulting organic layer was dried over anhydrous MgSO4. The solvent was evaporated, yielding a solid white product that matched the published spectrum36. To make 1a, 9-phenyl-10-methylacridin-9-ol (0.25 g, 0.87 mmol) and a magnetic stir bar were added to a dry 15-ml vial that was purged with Ar. The 9-phenyl-10-methylacridin-9-ol was dissolved under stirring in dry Et2O at room temperature. Triflic acid (0.082 ml, 0.97 mmol, 1.1 equiv.) was added to the vial and the mixture was stirred for an additional 30 min and then chilled to 0 °C. The precipitate was filtered, washed with anhydrous Et2O and dried in vacuum to give a solid product. The 1H NMR spectrum of 1a matched the previously published spectrum36.
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