A kind of 5-hydrogen-1,4-benzodiazepine compound and its synthesis method
A technology of benzodiazepine and synthesis method, applied in the field of heterocyclic compounds and synthesis thereof, can solve the problems of low yield, low reaction yield, low yield and the like, and achieves high product yield and simple reaction operation , the effect of cheap and easy-to-obtain raw materials
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[0032] A kind of 5-hydrogen-1 of the present invention, the synthetic route of 4-benzodiazepine compound is as follows figure 2 Shown; Its concrete synthetic method comprises the following steps:
[0033] (1) In the reaction device, sequentially add 1 to 50 mol% iodine elemental catalyst, 1,2-disubstituted acetylene compound and organic solvent, and react under heating at 50 to 140°C;
[0034] (2) After reacting for a period of time, add 2-aminobenzylamine compound and acidic compound successively, continue heating reaction;
[0035] (3) After the reaction is complete, the 5-hydrogen-1,4-benzodiazepines are obtained by column chromatography.
[0036] In step (1), the reaction temperature can be selected to be 80-140°C, and generally 130°C is more selected during the reaction process; in step (2), the reaction temperature can be selected to be 80-120°C, generally during the reaction The process would be more preferably 100°C.
Embodiment 1
[0039] The synthesis of 2,3-bis(4-methylphenyl)-5-hydrogen-1,4-benzodiazepine (compound 1), its structural formula is:
[0040]
[0041] Preparation method 1: Add 10.1 mg of iodine, 41.2 mg of 1,2-di(4-methylphenyl)acetylene, and 2 mL of dimethyl sulfoxide to the reaction tube in sequence, and react in an oil bath at 130°C for 24 hours. The reaction solution was cooled to room temperature, and then 97.7 mg of 2-aminobenzylamine and 1 mL of acetic acid were added in sequence, and placed in an oil bath at 100°C for 20 hours. Finally, 48.0 mg of compound 1 was obtained by conventional post-treatment, with a yield of 74%.
[0042] Preparation method 2: Add 12.9 mg of iodobenzene diacetate, 41.2 mg of 1,2-bis(4-methylphenyl)acetylene, and 2 mL of dimethyl sulfoxide to the reaction tube in sequence, and react in an oil bath at 130°C for 24 After 1 hour, the reaction solution was cooled to room temperature, and then 97.7mg of 2-aminobenzylamine and 1mL of acetic acid were added su...
Embodiment 2
[0048] The synthesis of 2,3-bis(4-ethylphenyl)-5-hydrogen-1,4-benzodiazepine (compound 2), its structural formula is:
[0049]
[0050] Into the reaction tube, add 10.1 mg iodine element, 46.8 mg 1,2-bis(4-ethylphenyl) acetylene, and 2 mL dimethyl sulfoxide in sequence, react in an oil bath at 130°C for 24 hours, and cool the reaction solution to At room temperature, 97.7 mg of 2-aminobenzylamine and 1 mL of acetic acid were added sequentially, and placed in an oil bath at 100°C for 20 hours. Finally, 55.0 mg of compound 2 was obtained by conventional post-treatment, with a yield of 78%.
[0051] Compound 2 has a melting point of 81-82°C.
[0052] The NMR characterization results of compound 2 are: 1 H NMR (400MHz, CDCl 3 ): δ 7.76(d, J=8.2 Hz, 2H), 7.50(d, J=7.8Hz, 1H), 7.45(d, J=8.2Hz, 2H), 7.36(t, J=8.0Hz, 1H) , 7.21-7.15(m, 3H), 7.05(d, J=8.1Hz, 2H), 4.81(d, J=10.6Hz, 1H), 3.95(d, J=10.6Hz, 1H), 2.64(q, J=7.6Hz, 2H), 2.55(q, J=7.6Hz, 2H), 1.21(t, J=7.6Hz, 3H), 1.13(...
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