Synthesis of aromatic and heteroaromatic annelated [1,4]diazepines

Abstract

4-Chlor-3-coumarincarbaldehyde 2 or 4-azido-3-coumarincarbaldehyde 3 are converted into 1,4-benzodiazepines 9-12 by nucleophilic substitution with diamines 4-7 and subsequent cyclization with good yields. Following the same methodologies, carbaldehydes 2 or 3 when treated with 2-aminophenol 8 afforded 4-(2′-hydroxyphenyl)-amino-3-coumarincarbaldehyde 13 in good yields.