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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.

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