Reaction of 4-aryl-2,3-dihydro-2-phenyl-1H-1,5-benzodiazepines with 2-chloroacetyl chloride. Synthesis of N-acyl- and azeto[1,2-a]-1,5-benzodiazepines

摘要

It was found that 2-chloroacetyl chloride 7 reacts primarily over the NE-group at position I of 1,5-benzodiazepines 6a-e in dry benzene at room temperature in the presence of TEA to render the N-acetylderivatives 8a-e in good yields. Subsequently, cycloaddition reaction of compounds 8a-e with 7 in dry benzene-TEA lead to the formation of the new azeto[1,2-a][1,5]benzodiazepines 9a-e in moderate yields, involving the imino (C=N) moiety at position 4. The structure of compounds 8a-e and 9a-e was assigned by H-1 and C-13 NMR spectra and 2D experiments.