Preparation method of benzofuran condensed seven-membered diazafluoran*ketone compound
A technology of benzofurazadiene and benzofuran, which is applied in the direction of organic chemistry, can solve the problems of limited preparation methods, long reaction time, and many reaction steps, and achieves wide applicability, short reaction time, and simple conditions Effect
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Embodiment 1
[0034] The synthetic method of compound a: add 37.5 mg of phenyl-substituted benzofurazadiene (0.1 mmol) and 24.2 mg of N-benzyloxy-2-bromoacetamide (0.1 mmol) in acetonitrile to form a reaction Then add 40mg of cesium carbonate (0.12mmol) to the reaction mixture, stir the reaction for 1h at 25°C to obtain the mixture, filter the mixture, wash with dichloromethane, combine the filtrates, evaporate the solvent under reduced pressure, and finally pass through silica gel Separation by column chromatography, the residue was eluted with petroleum ether and ethyl acetate at a volume ratio of 5:1, separated and purified to obtain 37 mg of 4-benzyloxy-5-phenyl-1-(4-toluenesulfonyl )-1,2,4,5-tetrahydro-3H-benzofuro[3,2-e][1,4]diazepine -3-ketone, yield 68%. Compound a is a white solid, mp 113-115°C.
[0035] Through hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry detection of compound a, the structural characteristic parameters are: (1) 1 H NMR (400MHz, CDC...
Embodiment 2
[0037] Synthetic method of compound b: Add 39.3 mg of 4-fluorophenyl substituted benzofurazepine (0.1 mmol) and 30 mg of N-benzyloxy-2- to N,N-dimethylformamide Bromoacetamide (0.12mmol) forms a reaction mixture, then 40mg of cesium carbonate (0.12mmol) is added to the reaction mixture, and the reaction is stirred at 25°C for 1h to obtain a mixture, the mixture is filtered and washed with dichloromethane, and the filtrates are combined , the solvent was evaporated under reduced pressure, and finally separated by silica gel column chromatography, and the residue was eluted with petroleum ether and ethyl acetate with a volume ratio of 5:1, and separation and purification were collected to obtain 46 mg of 4-benzyloxy-5-( 4-fluorophenyl)-1-(4-toluenesulfonyl)-1,2,4,5-tetrahydro-3H-benzofuro[3,2-e][1,4]diazepine -3-ketone, yield 82%. Compound b is a white solid, mp 114-116°C.
[0038] Through hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry detection of co...
Embodiment 3
[0040] Synthetic method of compound c: Add 40.9 mg of 4-chlorophenyl-substituted benzofurazepine (0.1 mmol) and 30 mg of N-benzyloxy-2-bromoacetamide (0.12 mmol) to acetonitrile Form a reaction mixture, then add 40 mg of cesium carbonate (0.12 mmol) to the reaction mixture, stir the reaction for 1 h at 25 ° C to obtain a mixture, filter the mixture, and wash with dichloromethane, combine the filtrates, evaporate the solvent under reduced pressure, and finally Separated by silica gel column chromatography, the residue was eluted with petroleum ether and ethyl acetate at a volume ratio of 5:1, separated and purified to obtain 45 mg of 4-benzyloxy-5-(4-chlorophenyl)-1 -(4-Toluenesulfonyl)-1,2,4,5-tetrahydro-3H-benzofuro[3,2-e][1,4]diazepine -3-ketone, yield 78%. Compound c is a white solid, mp 120-122°C.
[0041] Through hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry detection of compound c, the structural characteristic parameters are: (1) 1 H NMR (...
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