An efficient and improved procedure for the synthesis of 1,4-diazepine and 1,5-benzodiazepine derivatives via the reaction of ketimine intermediates with aldehydes in the presence of Keggin-type heteropolyacids (HPAs) was developed. High yields and short reaction times were obtained for both electron-releasing and electron-withdrawing substituted 1,4-diazepine and 1,5-benzodiazepines derivatives.
Reaction of pyrone 1a or tetronic acid 1b with o‐phenylenediamine derivatives gave enaminone compounds 2. When reacting with different electrophiles, these intermediates allowed versatile access to different heterocyclic structures: when DMA derivatives or triphosgene was used, cyclization occurred through nitrogen, leading to benzimidazoles 3 and benzimidazolones 4, respectively, while reaction with benzaldehyde yielded benzodiazepines 5.
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