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CAS No. : | 771-97-1 | MDL No. : | MFCD00004116 |
Formula : | C10H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XTBLDMQMUSHDEN-UHFFFAOYSA-N |
M.W : | 158.20 | Pubchem ID : | 69872 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.76 |
TPSA : | 52.04 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.17 cm/s |
Log Po/w (iLOGP) : | 1.35 |
Log Po/w (XLOGP3) : | 1.54 |
Log Po/w (WLOGP) : | 2.02 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 1.53 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.41 |
Solubility : | 0.619 mg/ml ; 0.00391 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.24 |
Solubility : | 0.906 mg/ml ; 0.00573 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.34 |
Solubility : | 0.072 mg/ml ; 0.000455 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P201-P264-P280-P308+P313-P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319-H351 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With hydrogenchloride; ammonia; ammonium chloride In ethanol for 6 h; Reflux | Compound 1 (2 gm) was dissolved in absolute ethanol. Ammonium chloride (1.5 gm),dil. HCl (in catalytic amount) and excess of strong ammonium solution were added to it and reuxed for 6 h on water bath till appearing of permanent dark greenish colour. After completion of reaction, solution was cooled and kept in deep freezer for overnight. Greenish crystals were fltered, dried and recrystallized with methanol. Dark greenish crystals;Yield 75percent; Rf 0.89, Rf 0.82; mp 150 °C; IR (νmax,KBr, cm-1): 758, 854, 1473 (aromatic =C-N), 1500(aromatic C=C), 1681 (N-H), 3049 (N-H); 1H-NMR(CDCl3 500 MHz): 7.45-7.46 (dd, J=3.5-4 Hz, 2H,Ar-H), 7.12-7.14 (dd, J=3-3.5 Hz, 2H, Ar-H), 7.09 (s,Ar-H, 2H), 7.05 (s, Ar-NH2,4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol; at 85℃; for 4.5h;Inert atmosphere; | lH-naphtho[2,3-d] imidazole (8). According to a previously described method, (Herbert et al., 1987; Sachs, 1909) a mixture of diaminonaphthalene (1.015 g, 6.416 mmol), formic acid (4.9 mL, 130 mmol), and ethanol (10 mL) was refluxed at 85 C under N2 for 4.5 h. The reaction mixture was basified to pH 8 by dropwise addition of pH 13 ammonium hydroxide solution (about 10 mL). The precipitated brown solid was filtered off and washed with diethyl ether (ether washes were concentrated and resuspended to produce another batch of gold-colored product), to yield ExBIM (786 mg, 73% yield). NMR (MeOH-d4): 8.39 (s, 1H), 8.08 (bs, 2H), 7.97 (m, 2H), 7.39 (m, 2H). 13C NMR (MeOH-d4): 146.99, 132.08, 129.03, 125.03. ESI-MS: M+H+ calc'd 169.0760, found 169.0760. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In ethanol; at 80℃; for 5h;Reflux; | Procedure: 1.9g (12mmol) 2,3- diaminonaphthalene and 1.9g (12mmol) was dissolved in 60mL naphthoquinone anhydrous ethanol, stirred at reflux for 5 hours. Cool to room temperature, filtered, discard the cake. / 87% Column chromatography with petroleum ether / methylene chloride solvent system as eluent to give a yellow solid, yield 87% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydrogenchloride; cetyltrimethylammonim bromide; In ethanol; water; at 35℃; for 0.166667h; | In a 100 ml beaker, 2 mmol of Benzil, 2mmol of CTAB were added to 10 ml Ethanol andplaced on a magnetic stirrer cum temperaturebath at stirring speed of 750 rpm at 35 0C, a littlehigher than room temperature. A mixture of 10 mlof 2, 3-diaminonapthalene dissolved in 1M HCl wasadded in-situ to this reaction mixture drop by drop. Apale brown coloured precipitate was obtained after10 minutes. The precipitate was filtered usingWhatmann 40 flter paper and subsequently driedunder shadow. The precipitate was re-crystallizedwith ethanol. This re-crystallized yield was used asa source for further TLC and HPLC chromatographicstudies followed by spectroscopic characterization.The structure of the resulting compound was asshown in the Figure 1. procedure for the synthesis of 2, 3-diphenylbenzo [g] quinoxalineIn a 100 ml beaker, 2 mmol of 1,2-diphenylethane-benzil, 2 mmol of CTAB were added to 10 mlEthanol and placed on magnetic stirrer, added with 2mmol of <strong>[771-97-1]2,3-diaminonaphthalene</strong> in 10 ml 1M HCl,in-situ to this reaction mixture, drop by drop. Theprecipitate was re-crystallized with ethanol. Characterization of 2, 3-diphenyl benzo [g]quinoxalineyield= 97%: Pale Brown coloured crystals:m.p. = 99C; FTIR: Heterocyclic -C=N & -C=Cstr.=1595.13 cm-1, aromatic -CH str.=3061.03 cm-1,aromatic -C=C- str.=1666.50 cm-1, aromatic -C-Cstr.=1517.98 cm-1, aromatic -C-N- str. = 1325.10cm-1; H1NMR : (400 MHz, DMSO): d = 7.946-7.925(J = 1.9622) (t, 2H, arom.); d =7.829-7.791 (J =1.000) (t, 2H, arom.); d = 7.660-7.621 (J = 2.0311) (t,4H, arom.); C13NMR: (400 MHz, DMSO) d = 194.79,135.50, 132.25, 129.66, 129.56, 129.48, 128.39,128.01, 127.11, 40.18, 39.97, 39.76, 39.55, 39.34,39.14, 38.93 ppm. |
72% | In ethanol; for 2h;Reflux; | Equimolar quantities of compound 2(0.001 mol) and benzil (0.001 mol) were dissolved in ethanol (30 mL) and reuxed for 2 h. After completion of reaction, reaction mixture was cooled, kept for overnight, yellow crystalline solid was fltered, dried and recrystallized with ethanol : methanol (1:1) mixture. Yellow crystalline solid; Yield 72%; Rf 0.83;mp 170 C; IR (numax,KBr, cm-1) : 725, 785, 820, 875,1475, 1510 (aromatic C=C), 1660 (quinoxalineC=N); 1H-NMR (DMSO-d6 500 MHz) d: 8.73-8.77 (m,J=2.5-4 Hz, 10H, Ar-H), 8.28 (s, 2H, Ar-H), 8.03-8.07(m, 4H, J=2.5-4 Hz, Ar-H). |
72% | In ethanol; for 2h;Reflux; | Equimolar quantities of compound 2 (0.001 mol) and benzil (0.001 mol) were dissolved in ethanol (30 mL) and refluxed for 2 h. Reaction solution was cooled and kept for overnight. Yellow crystalline solid was filtered, dried and recrystallized with ethanol:methanol solution (1:1). Yellow crystalline solid; yield 72%; Rf 0.83; mp 170C; IR (vmax, cm-1): 725 (mono-substituted aromatic ring), 785, 820, 875, 1475, 1510, 1660 (quinoxaline C=N); 1H-NMR (DMSO-d6, 500 MHz, delta): 8.73-8.77 (m, J=2.5-4 Hz, 10H, Ar-H), 8.28 (s, 2H, Ar-H), 8.03-8.07 (m, J=2.5-4 Hz, 4H, Ar-H). |
64% | With acetic acid; In ethanol; for 24h;Schlenk technique; Inert atmosphere; Reflux; | To a stirred solution of benzil (322 mg, 1.6 mmol) in ethanol(15 mL) was added <strong>[771-97-1]2,3-diaminonaphthalene</strong> (250 mg, 1.6 mmol)and acetic acid (0.5 mL). The reaction mixture was heated at refluxunder a nitrogen atmosphere for 24 h. The reaction mixture wascooled to room temperature and a precipitate collected by filtration to give L1 as a brown solid (0.34 g, 64%). 1H NMR (300 MHz, CDCl3):dH 8.68 (s, 2H, CH), 8.05 (dd, J 3.21 Hz, 6.39 Hz, 2H), 7.50 (m, 6H),7.30 (m, 6H) ppm. 13C{1H} NMR (101 MHz, CDCl3): dC 154.2, 139.2,138.0, 134.1, 129.8, 129.0, 128.6, 128.3, 127.6, 126.8 ppm. HRMSfound m/z 333.1387; calcd m/z 333.1386 for C24H16N2. UV-vis.(CHCl3) lmax (epsilon/dm3 mol1 cm1): 386 (25200), 309 (71500), 276(114100) nm. Selected IR (solid) ymax 1607, 1508, 1441, 1346, 1248,1175, 1013, 976, 876, 836, 760, 741, 691, 552, 500.0, 490, 467 cm1. |
46% | With iodine; In acetonitrile; at 20℃; | Benzil (3 mmol), <strong>[771-97-1]2,3-diaminonaphthalene</strong> (4.4 mmol), and iodine (0.37 mmol) were reacted in acetonitrile (10 mL) at room temperature. The precipitates were extracted with ether after adding into water. The residue evaporated in vacuum was purified using silica gel chromatography in ethyl acetate/hexane (1:20), and further purified by recrystallization in dichloromethane/hexane (1:1) using a slow evaporation method at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With Sucrose In water at 20℃; for 72h; | |
78% | In methanol for 0.116667h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With acetic acid; In ethanol; for 24h;Schlenk technique; Inert atmosphere; Reflux; | General procedure: To a stirred solution of benzil (322 mg, 1.6 mmol) in ethanol(15 mL) was added <strong>[771-97-1]2,3-diaminonaphthalene</strong> (250 mg, 1.6 mmol)and acetic acid (0.5 mL). The reaction mixture was heated at refluxunder a nitrogen atmosphere for 24 h. The reaction mixture wascooled to room temperature and a precipitate collected by filtration to give L1 as a brown solid (0.34 g, 64%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In ethanol for 1h; Reflux; Inert atmosphere; | |
80% | In toluene for 1h; Reflux; | |
77% | In ethanol for 0.5h; Heating; |
45.3% | In ethanol for 4h; Reflux; | |
In ethanol for 12h; reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; cetyltrimethylammonim bromide; In ethanol; water; at 35℃; for 0.166667h; | General procedure: In a 100 ml beaker, 2 mmol of Benzil, 2mmol of CTAB were added to 10 ml Ethanol andplaced on a magnetic stirrer cum temperaturebath at stirring speed of 750 rpm at 35 0C, a littlehigher than room temperature. A mixture of 10 mlof 2, 3-diaminonapthalene dissolved in 1M HCl wasadded in-situ to this reaction mixture drop by drop. Apale brown coloured precipitate was obtained after10 minutes. The precipitate was filtered usingWhatmann 40 flter paper and subsequently driedunder shadow. The precipitate was re-crystallizedwith ethanol. This re-crystallized yield was used asa source for further TLC and HPLC chromatographicstudies followed by spectroscopic characterization.The structure of the resulting compound was asshown in the Figure 1. |
71% | With acetic acid; In ethanol; for 24h;Schlenk technique; Inert atmosphere; Reflux; | General procedure: To a stirred solution of benzil (322 mg, 1.6 mmol) in ethanol(15 mL) was added <strong>[771-97-1]2,3-diaminonaphthalene</strong> (250 mg, 1.6 mmol)and acetic acid (0.5 mL). The reaction mixture was heated at refluxunder a nitrogen atmosphere for 24 h. The reaction mixture wascooled to room temperature and a precipitate collected by filtration to give L1 as a brown solid (0.34 g, 64%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; at 80℃; for 5h;Reflux; | Procedure: 1.66g (10.5mmol) of 2, 3_ diamino naphthalene and 1.48g (IOmmol) 1-phenyl-1,2-propanedione was dissolved in 30mL of anhydrous ethanol, stirred at reflux for 5 hours. /=12/180% After cooling to room temperature, the resulting solution was concentrated, column chromatography with petroleum ether / ethyl acetate = 12/1 as eluent to give a yellow solid powder with a yield of 80%. |
80% | In ethanol; for 5h;Reflux; | 1.66 g (10.5 mmol) of <strong>[771-97-1]2,3-diaminonaphthalene</strong> and 1.48 (10.0 mmol)1-phenyl-1,2-propanedione is dissolved in 30 ml of absolute ethanol,Stirring was carried out for 5 hours under reflux.After cooling to room temperature, the resulting solution was concentrated.Column chromatography separation,With petroleum ether / ethyl acetate = 12 / 1 as the eluent,Made a yellow solid powder,The yield is 80%,The compound intermediate A1 was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With zinc diacetate; In chlorobenzene; for 10h;Inert atmosphere; Reflux; | General procedure: Into a solution of bis-alpha-diketone C (0.50 mmol) in chlorobenzene (12.5 mL) containing a catalytic amount of zinc acetate was added o-phenylenediamine (1.10 mmol) under reflux for hours, monitored by TLC and 1H NMR. The reaction mixture was filtered to remove salt and the filtrate was concentrated. The residue was purified via recrystallization from EtOH/CHCl3 (3/2 by vol) to afford pure adduct. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With bromine; acetic acid; at 20℃; for 2h; | A mixture of 2.40mL of bromine (9.60g, 60.0mmol) and 30mL of glacial acetic acid was added dropwise into a solution of naphthalene-2,3-diamine (2.00g, 12.6mmol) in 100mL of glacial acetic acid, with vigorous stirring at room temperature. After 2h, the precipitate was filtered off and washed subsequently with aqueous K2CO3 solution and water. A brown powder was obtained after drying (3.33g, 10.1mmol, 85%). 1H NMR (400MHz, CDCl3, delta/ppm): 8.00-8.02 (2H, m), 7.38-7.40 (2H, m), 2.79 (4H, s). MS (EI): m/z 316. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With gallium(III) triflate In dichloromethane at 120℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88.5 percent / Br2 / acetic acid / 1 h / 20 °C 2: 91 percent / SeO2 / H2O; ethanol / 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The title compound was synthesized according to a literature procedure.3 Hexaketocyclohexane octahydrate (534 mg, 1.71 mmoles) and 2,3-diaminonaphthalene SM13 (1.00 g, 5.65 mmoles) were refluxed in 200 ml of glacial acetic acid at 140 C overnight. The reaction mixture was then filtered and washed with 6No.50 ml of hot glacial acetic acid. The solid was then refluxed with 200 ml of 30% nitric acid for 3 hours at 120 C. The dark brown solid (1.55 g, theoretical yield is 915 mg; therefore, impurities present) was filtered and dried under vacuum. This compound is insoluble in most organic solvents. MALDI- TOF MS (M+H): m/z 535.16, calcd for C36H19N6, 535.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol | 5.23 5.23. 5.23. Synthesis Of 2-phenyl-1,4-diaza-anthracene A preferred method of synthesis of 2-phenyl-1,4-diaza-anthracene (Compound 23) is as follows: 20 ml of ethanol containing 0.47 grams of 2,3-diaminonaphthalene and 0.47 grams of phenyl glyoxal hydrate were refluxed for 1.5 hour. Cooling and filtering gave 0.5 g (65%) of a light brown solid with a melting point of 163° C. The product gave the following analytical data: NMR (CDCl3): δ 9.38 (1H, l.c., H2), 8.71, 8.67 (2H, 2d, H5, 10), 8.25, 8.10 (4H, AA'BB'm, H6-9), 7.58 (5H, m, Ph). MS m/e 256 (M+, 100%), 229 (M-CN, 12%), 126 (71%) m/e. | |
In ethanol | 23 5.23. 5.23. Synthesis Of 2-phenyl-1,4-diaza-anthracene A preferred method of synthesis of 2-phenyl-1,4-diaza-anthracene (Compound 23) is as follows: 20 ml of ethanol containing 0.47 grams of 2,3-diaminonaphthalene and 0.47 grams of phenyl glyoxal hydrate were refluxed for 1.5 hour. Cooling and filtering gave 0.5 g (65%) of a light brown solid with a melting point of 163° C. The product gave the following analytical data: NMR (CDCl3): δ 9.38 (1H, l.c., H2), 8.71, 8.67 (2H, 2d, H5,10), 8.25, 8.10 (4H, AA'BB'm, H6-9), 7.58(5H, m, Ph). MS m/e 256 (M+, 100%), 229 (M--CN, 12%), 126(71%) m/e. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With air; iodine; acetic acid at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With toluene-4-sulfonic acid In neat (no solvent) at 20℃; for 4h; Milling; Green chemistry; | |
40% | With pyridine at 120℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With iodine In water; acetic acid at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With [ς:η1:η5-(OCH2)(Me2NCH2)C2B9H9]Ti-(NMe2) In toluene at 115℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With oxygen; triethylamine; In toluene; at 60℃; under 760.051 Torr; for 12h; | Typical procedure: Mix Et3N (2.53 mg, 0.025 mmol), 2-phenylacetaldehyde 1a (30 mg, 0.25 mmol), benzene-1,2-diamine 2a (32.4 mg, 0.3 mmol), in toluene (2.5 mL) under O2 (1 atm). The reaction mixture was stirred at 60 C for 12 h. After cooling down to room temperature and concentrating in vacuum, the residue was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate=20:1) to afford 47 mg (91%) of 3aa. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In diethylene glycol dimethyl ether; at 140℃; for 24h; | A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 C in a siliconebath that contains a magnetic stirrer and a temperature controller. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In acetonitrile; at 200℃; under 12929 Torr; for 0.583333h;Microwave irradiation; | General procedure: Ethyl-2-oxo-2-(6-phenylimidazo[2,1-b]thiazol-5-yl)acetate (4a,0.3 g, 0.9 mole) and O-phenylenediamine (5a, 0.108 g, 0.9 mole) were mixed properly and was charged into a specially designed microwave test tube and acetonitrile (5 mL) was added to this mixture and was irradiated for 35 min at 200C and 250 psi pressure. After cooling, the solid mass was crushed into 50 ml cold acetonitrile. The solid mass was filtered and the filtrate was discarded. After washing several time with cold acetonitrile, the solid mass was dried under vacuum to get the 3-(6-Phenylimidazo[2,1-b]thiazol-5-yl)quinoxalin-2(1H)-ones (6a). The related compounds (6b-q) were prepared in the same way |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In acetonitrile; at 200℃; under 12929 Torr; for 0.583333h;Microwave irradiation; | General procedure: Ethyl-2-oxo-2-(6-phenylimidazo[2,1-b]thiazol-5-yl)acetate (4a,0.3 g, 0.9 mole) and O-phenylenediamine (5a, 0.108 g, 0.9 mole) were mixed properly and was charged into a specially designed microwave test tube and acetonitrile (5 mL) was added to this mixture and was irradiated for 35 min at 200C and 250 psi pressure. After cooling, the solid mass was crushed into 50 ml cold acetonitrile. The solid mass was filtered and the filtrate was discarded. After washing several time with cold acetonitrile, the solid mass was dried under vacuum to get the 3-(6-Phenylimidazo[2,1-b]thiazol-5-yl)quinoxalin-2(1H)-ones (6a). The related compounds (6b-q) were prepared in the same way |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In acetonitrile; at 200℃; under 12929 Torr; for 0.583333h;Microwave irradiation; | General procedure: Ethyl-2-oxo-2-(6-phenylimidazo[2,1-b]thiazol-5-yl)acetate (4a,0.3 g, 0.9 mole) and O-phenylenediamine (5a, 0.108 g, 0.9 mole) were mixed properly and was charged into a specially designed microwave test tube and acetonitrile (5 mL) was added to this mixture and was irradiated for 35 min at 200C and 250 psi pressure. After cooling, the solid mass was crushed into 50 ml cold acetonitrile. The solid mass was filtered and the filtrate was discarded. After washing several time with cold acetonitrile, the solid mass was dried under vacuum to get the 3-(6-Phenylimidazo[2,1-b]thiazol-5-yl)quinoxalin-2(1H)-ones (6a). The related compounds (6b-q) were prepared in the same way |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N?-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; phenylsilane; In tetrahydrofuran; at 70℃; under 750.075 - 2250.23 Torr; for 24h;Schlenk technique; Inert atmosphere; Glovebox; | General procedure: A-Synthesis of Benzimidazole and Derivatives from Aromatic 1,2-DiaminesThe first results presented describe the synthesis of benzimidazole rings and derivatives from aromatic 1,2-diamines. In this case, the amine R1NH2 and the nitrogenous nucleophilic agent R5R6NH are two reactive functional groups of one and the same molecule (diamine) and are thus connected via a covalent bond. This bond is preferably an aromatic ring of benzene, pyridine or pyrimidine type and the ring formed during the reaction is a nitrogenous heterocycle comprising 5 atoms of imidazole type. In the case where the nucleophile is oxygen-based (R7OH), the rings obtained are benzoxazoles. The results presented were produced by preferably using two sources of different reducing agents, polymethylhydrosiloxane (PMHS), sold by Aldrich under the reference 176206, and phenylsilane (PhSiH3), sold by Aldrich. In the case of the PMHS, as a silane is a polymer, the number of equivalents introduced is given with respect to the number of hydrides introduced and thus the number of monomers introduced with respect to the amine. Thus, the introduction of 3 equivalents of PMHS corresponds to the introduction of 3 equivalents of hydride and thus 3 equivalents of monomers of the PMHS with respect to the amine. Different (pre)catalysts were tested for the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 20℃; for 5h;Inert atmosphere; Schlenk technique; | <strong>[771-97-1]2,3-Diaminonaphthalene</strong>(0.3164g, 2mmol), bromobenzene(0.6281g, 4mmol), Pd2(dba)3(0.0916g)(Pd%=21.5%), BINAP(0.0934g), NaOtBu (0.5766g, 6mmol) and toluene(3ml) were added in a Schlenk flask under N2. The mixture stirred at room temp for 5 hours. The reaction was monitored by TLC. After the reaction was completed, the reaction mixture was cooled to room temp and quenched by addition of sat. NH4Cl, then extracted into EA. The organics were washed with brine and dried over Na2SO4, filtered and concentrated to yield the crude product. The product was purified by silica flash column chromatography. Yield=0.323g 52%. 1H NMR (CDCl3): delta 7.67 (s, 2H); 7.63 (dd, 2H); 7.31 (m, 6H); 7.1 (dd, 4H); 7.01 (td, 2H); 5.84 (s, 2H); 13C NMR (CDCl3): delta 143.64; 135.32; 130.46; 129.48; 126.41;124.43; 121.29; 118.11; 115.11. MS(ESI)m/z: 311.1[M+H]+. HRMS [M]+ calcd, 310.1470; found, 310.1475. |
52% | With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 110℃;Inert atmosphere; | 2. 3 - diamine naphthalin from (3.164g, 20mmol), bromophenylacetic(6.281g, 40mmol), Pd2 (dba) 3(0.916g, 1mmol) (reagent is Pd content of 21.5%), BINAP (0.934g, 7.5% eq), sodium tertiary butyl alcohol (5.766g, 3eq) and anhydrous toluene (20 ml) is added to the protection of nitrogen in the reaction pipe, temperature 110 C. Reaction sleepovers. Reaction with filter paper out solid, and the solid is washed with ethyl acetate, the obtained liquid merger, turns on lathe does , column to the product is a white solid 3.228g, yield 52%. |
48% | With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In water; toluene; for 20h;Inert atmosphere; Reflux; | a) Synthesis of N2,N3-diphenylnaphthalene-2,3-diamine A mixture of 25 g (0.16 mol) of <strong>[771-97-1]2,3-diaminonaphthalene</strong>, 49.6 g (0.32 mol) of bromobenzene and 250 ml of toluene is degassed under vacuum and backfilling with argon (repeated three times). 1 .45 g (1.58 mmol) of dipalladium tris(dibenzylidene acetonate), 2.74 g (4.74 mmol) ofXantPhos ligand (= 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene), 21.0 g sodium teflbutoxide (0.22 mol) and 2.84 ml of degassed water are added and the mixture degassed again 3 times with vacuum I argon backfilling. The dark suspension is refluxed under argon for 20 hours and cooled to room temperature. The mixture is diluted with 400 ml of dichloromethane, extracted twice with a 1 % aqueous solution of sodium cyanide, washed three times with water,dried over sodium sulfate, and concentrated under vacuum. The residue is purified by chromatography (silica gel, dichloromethane 99.5% : triethylamine 0.5%) to give the title product as a brown powder (yield: 23.5 g (48%)).1HNMR (300 MHz, CDCI3): = 7.67 (s, 2H), 7.64-7.60 (m, 2H), 7.37-7.27 (m, 6H), 7.10 (m, 4H), 7.00 (tt, 2H), 5.84 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With phosphoric acid at 20 - 165℃; for 8h; Inert atmosphere; | 6.2. Standard procedure 1 for the preparation of 3-(benzimidazol-2′-yl)coumarins (3a-m) General procedure: To a solution containing of 1,2-phenylenediamines 1 (1.0equiv) and 3-ethoxycarbonylcoumarins 2 (1.0equiv) were added o-phosphoric acid (85%, 15-16equiv). The reaction mixture was stirred at room temperature for 5.0min and at 165°C for another 8.0h. Then the solution was permitted to cool down to 100°C and poured in a large volume (500mL for 0.20mol of coumarin ester) of stirred water. The solution was neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (3×15mL). The combined organic layers were washed with brine (15mL), dried over MgSO4 (s), filtered, and concentrated under reduced pressure to provide crude solids, which were then recrystallized in EtOH to give the pure coumarins 3a-m in 40-67% yields with purity >99.6%, as checked by GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With acetic acid; In water; at 200℃; for 0.05h;Microwave irradiation; | General procedure: Acetonedicarboxylate (1.5mmol), 1,2-aryldiamine 1 (1.0mmol), water (5mL) and two drops of acetic acid were mixed thoroughly and were irradiated in a Biotage Initiator 2.0 microwave oven at 200C for 3min. The crude product was filtered by Gooch funnel, washed on the funnel with diethyl ether and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With acetic acid; In water; at 200℃; for 0.05h;Microwave irradiation; | General procedure: Acetonedicarboxylate (1.5mmol), 1,2-aryldiamine 1 (1.0mmol), water (5mL) and two drops of acetic acid were mixed thoroughly and were irradiated in a Biotage Initiator 2.0 microwave oven at 200C for 3min. The crude product was filtered by Gooch funnel, washed on the funnel with diethyl ether and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triphenylantimony; In dichloromethane; at 20℃; for 24h; | General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822: |
69% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 110℃; for 0.5h;Microwave irradiation; | General procedure: 2-hydroxyacetophenone (0.068g, 0.50mmol), o-phenylenediamine (0.054g, 0.50 mmol), copper acetate monohydrate (10mg, 0.050mmol) and TEMPO (7.8mg, 0.050 mmol) were dissolved in DMF (2 ml) in a microwave tube equipped with a stirrer bar. The mixture was irradiated for 30 minutes at 110 C under open vessel conditions. Water was added to the mixture and the resulting solution was then extracted with dichloromethane and concentrated to produce the crude product, which was subsequently purified using radial chromatography to produce the title compound as an orange solid (0.097g, 94%) mp = 80 - 81C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In butan-1-ol; for 12h;Inert atmosphere; Reflux; | A reaction mixture consisting of 2,3-diaminonaphthalene (0.75g, 4.74mmol), 3,4-dihydro-2H-pyran-5-carbaldehyde (0.53g, 4.74mmol) and n-butanol (15mL) was refluxed under argon for 12h. A red, fairly insoluble precipitate was filtered off and washed thoroughly with ethanol and diethyl ether. Red microcrystals, yield 0.25g (42%), mp 312-316C (decomposition). Analytical sample was recrystallized from DMF. Crystals suitable for X-ray measurements were grown from DMF. 1H NMR (300MHz, DMSO-d6, delta ppm): 1.76 (m, 4H, CH2CH2O), 2.46 (m, 4H, CH2), 3.54 (m, 4H, CH2O), 4.51 (t, J=5.0Hz, 2H, OH), 7.31 (m, 4H, Ar-H), 7.72 (m, 4H, Ar-H), 7.85 (s, 4H, H1,6,12,17), 8.26 (d, J=6.0Hz, 4H,=CHN), 12.72 (t, J=6.0Hz, 2H, NH); 13C NMR (75MHz, DMSO-d6, delta ppm): 28.78 (CH2CH2O), 35.34 (CH2), 59.87 (CH2O), 108.86, 109.88, 124.82, 126.89, 131.05, 136.91 (Caromat.N), 148.47 (=CHN); IR (ATR) numax(cm-1): {3372, 3311} (OH), {3194, 3176} (NH), 3053 (Ar-H), {2941, 2928, 2872} (CH2), {1640, 1620, 1596, 1547} (C=N, Ar), 1297, 1272 (C-O); ESI-MS: (m/z) 505.4 (M+H+); Anal. Calcd for C32H32N4O2: C, 76.16; H, 6.39; N, 11.10. Found: C, 75.80; H, 6.45; N, 11.15%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium metabisulfite; In N,N-dimethyl-formamide; at 120℃; | General procedure: A solution of substituted o-phenyldiamine (1.0 equiv), thiazole-4-aldehyde or pyridine-2-aldehyde (1.0 equiv) with sodium pyrosulfite in DMF was stirred at 120° C overnight. On completion of the reaction monitored by TLC, the solvent was evaporated and the residue was purified by silica gel chromatography by DCM/MeOH system to afford the final product. If necessary, the crudeproduct could be recrystallized in DCM or dichloroethane to afford pure sample. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic acid for 4h; Reflux; | Preparation of 3-Chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (6c) and 3-Chloro-7H-benzo[de]naphtho[20,30:4,5]imidazo[2,1-a]isoquinolin-7-one (6d) General procedure: 4-Chloronaphthalene anhydride (4e) (0.01 mol) and phenylene-1,2-diamine (5h) (0.01 mol) or naphthalene-2,3-diamine (5i)(0.01 mol) were dissolved in acetic acid (100 mL) and the mixture was stirred and heated under reflux for 4 h. The mixture was allowed to cool to room temperature and the resulting precipitate was filtered off, washed with acetic acid, and dried ina vacuum desiccator. The target compounds were purified bysilica gel column chromatography (eluent: petroleum ether/dichloromethane/ethyl acetate with increasing polarity) followedby recrystallisation from toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bromine; acetic acid / 2 h / 20 °C 2: thionyl chloride; pyridine / chloroform / Cooling with ice; Reflux | ||
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: thionyl chloride; pyridine / chloroform | ||
Multi-step reaction with 2 steps 1: bromine; acetic acid / 6 h / 20 °C 2: pyridine; N-phenylsulfinylamine; chloro-trimethyl-silane / acetic anhydride / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With Imidazole hydrochloride; at 120℃; for 6h; | General procedure: To a 10mL three-necked round bottle was charged with 1a (0.54 g, 5 mmol), imidazolium chloride (0.09 g, 0.5 mmol) and N,N-dimethylformamide 2 mL. The resulting solution was warmed to120 C and stirred at this temperature for 6 h. When the reaction was completed, 25 mL water was added and the resulting mixture was extracted with 25 mL ethyl acetate twice. The combined organic layer was successively washed with H2O (50 mL) and then brine (50 mL), then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate or recrystallized from petroleum ether/EA to give the title products. |
45% | With zinc(II) acetate dihydrate; In neat (no solvent); at 120℃; under 7600.51 Torr; for 18h;Autoclave; Inert atmosphere; Green chemistry; | General procedure: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | With acetic acid; for 3h;Reflux; | A mixture of 4,4?-dibromobenzil (3.680 g, 10 mmol)and 2,3-diaminonaphthalene (1.582 g, 10 mmol) was dissolved in 20mL of glacial acetic acid and refluxed for 3 h. The reaction mixture was allowed to cool and then poured over crushed ice to obtain the light green coloured solid. The obtained solid was then dried under vacuum and purified using column chromatography (eluent: n-hexane: chloroform ratio as70:30) to obtain a bright green solid. Yield: 4.429 g(90.4%), M.p.: 208C. IR (KBr numax cm-1): 3056, 2922, 2852, 1585 (-C=N str), 1068; 1H NMR (300 MHz,CDCl3): delta (ppm) 8.70 (s, 2H, ArH), 8.10 (dd, 2H,ArH, J = 3.3, 3.0 Hz), 7.41-7.58 (m, 10H, ArH,);13C NMR: 152.46, 137.77, 137.72, 134.23, 131.61,131.38, 128.53, 127.60, 126.96, 123.89. Anal.Calcd forC24H14Br2N2: C (58.81), H (2.88), N (5.71), Br (32.60).Found: C (58.79), H (2.86), N (5.74), Br (32.61). |
72% | With acetic acid; In ethanol; for 24h;Schlenk technique; Inert atmosphere; Reflux; | General procedure: To a stirred solution of benzil (322 mg, 1.6 mmol) in ethanol(15 mL) was added 2,3-diaminonaphthalene (250 mg, 1.6 mmol)and acetic acid (0.5 mL). The reaction mixture was heated at refluxunder a nitrogen atmosphere for 24 h. The reaction mixture wascooled to room temperature and a precipitate collected by filtration to give L1 as a brown solid (0.34 g, 64%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1,2-dimethyl-3-[4-(1,2-dimethyl-1H-imidazol-3-ium-3-yl)butyl]-1H-imidazol-3-ium dibromide; In neat (no solvent); at 20℃; for 2h;Green chemistry; | General procedure: Azo-linked salicylaldehydes 1 (2 mmol) and naphthalene-2,3-diamine or 1,2-diaminobenzene 2 (2 mmol) and [BDBDMIm]Br(0.04 mmol) was stirred at room temperature for the required reactiontime according to Table 3. After completion of reaction, thereaction product was extracted by CHCl3/H2O. After evaporation oforganic solvent, the crude product was released and recrystallizedfrom EtOH and dried to afford power compounds of 3a-j as purecrystalline products in 85e95% yields (Table 3).The identity and purity of the products were confirmed by IR, 1HNMR, 13C NMR and elemental analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1,2-dimethyl-3-[4-(1,2-dimethyl-1H-imidazol-3-ium-3-yl)butyl]-1H-imidazol-3-ium dibromide; In neat (no solvent); at 20℃; for 2h;Green chemistry; | General procedure: Azo-linked salicylaldehydes 1 (2 mmol) and naphthalene-2,3-diamine or 1,2-diaminobenzene 2 (2 mmol) and [BDBDMIm]Br(0.04 mmol) was stirred at room temperature for the required reactiontime according to Table 3. After completion of reaction, thereaction product was extracted by CHCl3/H2O. After evaporation oforganic solvent, the crude product was released and recrystallizedfrom EtOH and dried to afford power compounds of 3a-j as purecrystalline products in 85e95% yields (Table 3).The identity and purity of the products were confirmed by IR, 1HNMR, 13C NMR and elemental analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1,2-dimethyl-3-[4-(1,2-dimethyl-1H-imidazol-3-ium-3-yl)butyl]-1H-imidazol-3-ium dibromide; In neat (no solvent); at 20℃; for 1h;Green chemistry; | General procedure: Azo-linked salicylaldehydes 1 (2 mmol) and naphthalene-2,3-diamine or 1,2-diaminobenzene 2 (2 mmol) and [BDBDMIm]Br(0.04 mmol) was stirred at room temperature for the required reactiontime according to Table 3. After completion of reaction, thereaction product was extracted by CHCl3/H2O. After evaporation oforganic solvent, the crude product was released and recrystallizedfrom EtOH and dried to afford power compounds of 3a-j as purecrystalline products in 85e95% yields (Table 3).The identity and purity of the products were confirmed by IR, 1HNMR, 13C NMR and elemental analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iron(III) trifluoromethanesulfonate; In N,N-dimethyl-formamide; at 80℃; for 24h; | General procedure: A flask was charged with o-phenylenediamine (1a; 54 mg, 0.5 mmol), hexafluoroacetylacetone (2; 125 mg, 0.6 mmol), Fe(OTf)3 (25 mg, 0.05 mmol), DMF (2.0 mL). The reaction was stirred at 80 C for 24 h, when the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (10 mL) was added to the mixure, and then extracted with EtOAc (3×30 mL). The combined organic phase was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 3a (92 mg, 99%) as yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: NBS (214 mg, 1.2 mmol) was added to a solution of the appropriate alkyne 4 (1.0 mmol) in AcOH (8 mL) at r.t. The reaction mixture was stirred at reflux for 2 h, then the respective diamine 2 (1.1 mmol) was added to the reaction mixture directly. The mixture was stirred at 120 C for 2 h continuously, cooled to r.t., and the solvent was concentrated.The residue was diluted with aq NaHCO3 (95%, 10 mL) and the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford the crude product. Purification on silica gel (hexanes/EtOAc: 10:1to 6:1) afforded quinoxaline 5 or 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | General procedure: NBS (214 mg, 1.2 mmol) was added to a solution of the appropriate alkyne 4 (1.0 mmol) in AcOH (8 mL) at r.t. The reaction mixture was stirred at reflux for 2 h, then the respective diamine 2 (1.1 mmol) was added to the reaction mixture directly. The mixture was stirred at 120 C for 2 h continuously, cooled to r.t., and the solvent was concentrated.The residue was diluted with aq NaHCO3 (95%, 10 mL) and the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford the crude product. Purification on silica gel (hexanes/EtOAc: 10:1to 6:1) afforded quinoxaline 5 or 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | General procedure: NBS (214 mg, 1.2 mmol) was added to a solution of the appropriate alkyne 4 (1.0 mmol) in AcOH (8 mL) at r.t. The reaction mixture was stirred at reflux for 2 h, then the respective diamine 2 (1.1 mmol) was added to the reaction mixture directly. The mixture was stirred at 120 C for 2 h continuously, cooled to r.t., and the solvent was concentrated.The residue was diluted with aq NaHCO3 (95%, 10 mL) and the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford the crude product. Purification on silica gel (hexanes/EtOAc: 10:1to 6:1) afforded quinoxaline 5 or 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride; cetyltrimethylammonim bromide; In ethanol; water; at 35℃; for 0.166667h; | General procedure: In a 100 ml beaker, 2 mmol of Benzil, 2mmol of CTAB were added to 10 ml Ethanol andplaced on a magnetic stirrer cum temperaturebath at stirring speed of 750 rpm at 35 0C, a littlehigher than room temperature. A mixture of 10 mlof 2, 3-diaminonapthalene dissolved in 1M HCl wasadded in-situ to this reaction mixture drop by drop. Apale brown coloured precipitate was obtained after10 minutes. The precipitate was filtered usingWhatmann 40 flter paper and subsequently driedunder shadow. The precipitate was re-crystallizedwith ethanol. This re-crystallized yield was used asa source for further TLC and HPLC chromatographicstudies followed by spectroscopic characterization.The structure of the resulting compound was asshown in the Figure 1. |
In ethanol; at 85℃; for 12h;Inert atmosphere; | General procedure: Four phenylquinoxalines with thioether group (SQ), 2, 3-bis-(4-(phenylthio)phenyl)quinoxaline (SQ1), 2,2',3,3'-tetrakis- (4-(phenylthio)phenyl) -6, 60-biquinoxaline (SQ2), 2, 3-bis (4-(phenylthio)phenyl) benzo[g] quinoxaline (SQ3), and 2, 3-diphenyl-5, 6-bis (4-(phenylthio)phenyl) pyrazine (SQ4) were synthesized accordingto Scheme1, aswell as phenyl quinoxalines (Q) as reference. TakeSQ1 as example, 10mmol of benzene-1, 2-diamine and 10mmol 1,2-bis(4-fluorophenyl)- ethane-1, 2-dionewere dissolved in 20 mL of ethanol in 85 8C and stirred for 12 h under nitrogen protection. The mixture was then evaporated to remove most of the solvent and recrystallized. The precipitant was filtered from ethanol and dried to get 2,3-bis(4-fluorophenyl)quinoxaline (DF-Q). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triton X-100; In water; at 80℃; for 2h;Green chemistry; | General procedure: A mixture of beta-lapachone 2 (1.0 mmol), 2,3-diaminopyridine (1.0 mmol), triton X-100 (15 mol%), and distilled water (5.0 ml) were taken in a round-bottom flask. The reaction mixture was allowed to stir magnetically at 80 C for 2 h. Progress of the reaction was monitored by TLC. After completion of the reaction, the crude mass was obtained. The residue was purified over a column of silica gel (100-200 mesh) eluting with a mixture of hexane and ethyl acetate in different ratio, to yield regioisomers (4a and 4b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: 10 mL Pyrex tube equipped with a magnetic stir bar was charged with 1a (0.1 mmol), 10 mol % Cu(NO3)2·2.5H2O, CH3CN (2 mL) in air at 50 oC for 1 hour then the mixture followed by the addition of 2a (0.2 mmol) at room temperature for 2 h. Then mixture was evaporated under reduced pressure to remove the solvent and the residue was purified by flash chromatography on silica gel (Petroleum ether/ EtOAc) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; sodium acetate; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | <strong>[771-97-1]2,3-diaminonaphthalene</strong> (47.5 mg, 0.2 mmol),(Z)-2-bromocinnamaldehyde (64.7 mg, 0.3 mmol),a chiral triazole salt (8.4 mg, 0.02 mmol) as shown in formula III,Sodium acetate (33 mg, 0.4 mmol),Dichloromethane (2 mL) was placed in a 25 mL two-neck bottle.Reacted at room temperature under nitrogen for 24 h,The reaction solution was cooled and concentrated, and eluted with a mixed solvent of petroleum ether: ethyl acetate ratio of 3:1 as an eluent column chromatography, and the eluent fraction of all the products detected was collected.The solvent was evaporated to give the product 50 mg, yield 87%, 98.2% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.8% | 150 mL of absolute ethanol, 2,3-diaminonaphthalene (1.74 g, 11 mmol), 0.1 mL ofglacial acetic acid and activated molecular sieves (1.0 g) were successively added to a 500 mL threeneckedflask, and heated under reflux. Under the conditions of N2, a solution of 8-hydroxyjulolidine-9-formaldehyde (2.17 g, 10 mmol) in 80 mL of absolute ethanol was slowly added dropwise with aconstant pressure funnel. After the addition was completed, the reaction was continued for 24 hours.After the completion of the reaction, the activated molecular sieve was removed by hot filtration, andthe filtrate was evaporated to dryness to give a crude product. The crude product was crystallised fromanhydrous ethanol to afford crystals (yellow crystals of product III (AMHQ) 3.35 g, yield 93.8%, purity99.31%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With boric acid; In acetic acid; at 60℃; for 15h;Inert atmosphere; | General procedure: The corresponding diamine (1.5 mmol, 1 eq.) was mixed with alloxan monohydrate (0.21 g,1.5 mmol, 1 eq.) and boric acid (0.092 g, 1.5 mmol, 1 eq.) in glacial acetic acid (10 mL). The mixturewas stirred under an Ar atmosphere at 60 C for 15 h. The reaction mixture gradually turned into asuspension. The solid fraction was collected by ltration, washed with acetic acid (20 mL) and diethylether (20 mL). The crude product was purified by digestion in boiling methanol. Digested flavinderivative was further subjected to vacuum sublimation to yield the final target compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In methanol; at 75℃; for 12h;Inert atmosphere; Schlenk technique; Glovebox; | General procedure: 2-hydroxy-3-tert-butyl-5-R-benzaldehyde (10 mmol) was treatedwith corresponding diamines (4,5-dimethylbenzene-1,2-diamine forSD, 1,2-phenylenediamine for SP and 2,3-diaminonaphthalene for SNderivatives, 5.0 mmol, 0.5 equiv.) in methanol (20 mL) at 75 C. Thereaction mixture was stirred for 12 h, and then cooled to ambienttemperature, after which the mixture was filtered. Washing with methanolfollowed by drying in vacuo afforded the precursor ligands(SD1-SD6, SP1-SP6, and SN1-SN6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In methanol at 75℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; | General synthesis of Ar-{N]CH(C6H2-3-tBu-5-R)}2 (SD, SP, and SNseries). General procedure: 2-hydroxy-3-tert-butyl-5-R-benzaldehyde (10 mmol) was treatedwith corresponding diamines (4,5-dimethylbenzene-1,2-diamine forSD, 1,2-phenylenediamine for SP and 2,3-diaminonaphthalene for SNderivatives, 5.0 mmol, 0.5 equiv.) in methanol (20 mL) at 75 °C. Thereaction mixture was stirred for 12 h, and then cooled to ambienttemperature, after which the mixture was filtered. Washing with methanolfollowed by drying in vacuo afforded the precursor ligands(SD1-SD6, SP1-SP6, and SN1-SN6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In isopropyl alcohol; at 80℃; for 0.25h;Microwave irradiation; | General procedure: A mixture of o-phenylenediamine (1.0 mmol) and EDC.HCl (1.1 mmol) in 2-propanol (10 mL) was irradiated in microwave apparatus at 200 W (80 C) for 15 min. The reaction was monitored by TLC (eluent CH2Cl2 / MeOH 95:5). After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 25 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude product was purified by flash column chromatography using silica gel (100-200 mesh) with 1-5% MeOH/CH2Cl2 as eluent. The fractions containing product were collected and concentrated under reduced pressure to afford N-ethyl-1Hbenzo[d]imidazol-2-amine (1a, 90% yield) as an off white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In methanol; ethanol; at 80℃; for 24h; | In a 50 mL round bottom flask, 2,3-diaminonaphthalene (0.079 g, 0.5 mmol)And imidazole-2-carbaldehyde (0.1 g, 1.1 mmol) were dissolved in a mixed ethanol-methanol solvent (20 mL, v / v = 1: 1), and then 2-3 drops of acetic acid were added.The resulting mixture was heated to reflux (80 C), and it was continuously stirred for 24 hours, and then cooled to room temperature.The solid was filtered off, washed with CH3OH and dried under vacuum to obtain a yellow solid, which is the naphthalene derivative described in the present technology. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With iron(III) oxide; oxygen In N,N-dimethyl-formamide for 48h; Irradiation; | 29 Preparation of 2-butylbenzo[g]quinoxaline Take the quartz reaction tube, add a magnetic stirrer to it, then add 0.3mmol of 2,3-diaminonaphthalene, 0.6mmol of trihexylamine, 10mmol% of photosensitizer iron salt (Fe2O3), and finally add N, N -Dimethylformamide (DMF) 1mL.Then add a three-way gas head with a balloon on the top of the quartz reaction tube, first freeze the reaction stock solution completely with liquid nitrogen, then use an oil pump to vacuum the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under oxygen conditions, the reaction was carried out under blue LED light for 48 hours, the final product was detected by TLC, and finally 2-butylbenzo[g]quinoxaline was separated by column chromatography, and the yield was 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With oxygen; eosin y In dimethyl sulfoxide for 48h; Irradiation; | 28 Preparation of 2-propylbenzo[g]quinoxaline Take the quartz reaction tube, add a magnetic stirrer to it, then add 0.3mmol of 2,3-diaminonaphthalene, 0.6mmol of tripentylamine, 10mmol% of photosensitizer Eosin Y, and finally add dimethyl sulfoxide ( DMSO) 1mL.Then add a three-way gas head with a balloon above the quartz reaction tube, first freeze the reaction stock solution completely with liquid nitrogen, then use an oil pump to vacuum the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under oxygen conditions, the reaction was carried out under the light of incandescent lamp for 48 hours. The final product was detected by TLC, and finally separated by column chromatography to obtain the final product 2-propylbenzo[g]quinoxaline with a yield of 74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.1% | With sodium hydrogensulfite In N,N-dimethyl acetamide for 6h; Reflux; | 3.6.1. 2-(5-(1,10-Phenanthroline))-1H-naphtha[2,3]imidazole (pni) NaHSO3 (0.208 g, 2.0 mmol), 2,3-diaminonaphthalene (0.158 g, 1.0 mmol), and 1,10-phenanthroline-5-carbaldehyde (0.208 g, 1.0 mmol) were added to 10 mL dimethylacetamide.The solution was refluxed for 6 h. Then, 150 mL of water was added, yielding adark brown precipitate. Yield: 81.1%. Anal (%): ESIMS: m/z = 347 ([M + 1] +). 1H-NMR(400 MHz, ppm, DMSO-d6): 9.83 (d, 1H, J = 8.0 Hz), 9.21 (d, 2H, J = 4.0 Hz), 8.71 (s, 1H),8.63 (d, 1H, J = 8.0 Hz), 8.26 (s, 2H), 8.08 (dd, 2H, J1 = 4.0 Hz, J2 = 4.0 Hz), 7.93 (dd, 1H,J1 = 4.0 Hz, J2 = 4.0 Hz), 7.88 (dd, 1H, J1 = 4.0 Hz, J2 = 4.0 Hz), 7.43 (dd, 2H, J1 = 4.0 Hz,J2 = 4.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In decane; toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22.2 mg | Stage #1: (2E)-α-cyano-β-(p-chlorophenyl)ethenyl phenyl sulfone With Cumene hydroperoxide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea In toluene at -20℃; for 14h; Stage #2: 2,3-Diaminonaphthalene With triethylamine In toluene at 20℃; for 8.5h; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.3% | With sodium hydrogen sulphite In N,N-dimethyl acetamide at 140℃; for 4h; | 3.8.1. 2-(40-Methyl-bipyridine-4-yl)-1H-imidazo[4,5-b]Naphthalene (Mbin) 40-Methyl-2,20-bipyridine-4-carboxaldehyde [44] (0.198 g) and 2, 3-diaminonaphthalene(0.158 g) were dissolved in 15 mL dimethylacetamide. Then, NaHSO3 (0.208 g) was addedinto the solution. After reflux for 4 h, the addition of 200 mL water into the cooled solutiongave a dark brown precipitate. After filtration and water wash, the product was obtained.Further purification was performed by recrystallization in ethanol. Yield: 0.158 mg, 39.3%.Anal (%): (Found: N, 16.52; C, 78.67; H, 4.81%. Calcd for C22H16N4: N, 16.66; C, 78.55;H, 4.79%). ESI-MS: m/z = 336.2 ([M+1]+). 1H NMR (400 MHz, ppm, DMSO-d6): 13.52 (s, 1H), 9.26 (s, 1H), 8.92 (d, 1H, J = 4.0 Hz), 8.66 (d, 1H, J = 4.0 Hz), 8.34 (s, 2H), 8.28 (d, 2H,J = 4.0 Hz), 8.06 (m, 2H), 7.43 (m, 2H), 7.38 (d, 1H, J = 4.0 Hz), and 2.47 (s, 3H). |
Tags: 771-97-1 synthesis path| 771-97-1 SDS| 771-97-1 COA| 771-97-1 purity| 771-97-1 application| 771-97-1 NMR| 771-97-1 COA| 771-97-1 structure
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