Synthesis of Tetracyclic 8-Aza-Naphthalen-9-Ones and Oxa-Naphthalen-9-One

Abstract

Bromination of 1-methylbenzo[f]chromen-3-one with N-bromosuccinimide gives 2-bromo-1-methylbenzo[f]chromen-3-one which, on condensation with different primary aromatic amines, gives tetracyclic aza-naphthalen-9-ones. Condensation of 2-bromo-1-methylbenzo[f]chromen-3-one with different secondary cyclic amines also gives tetracyclic oxa-naphthalen-9-one. The formation of 8-aza-naphthalen-9-one and 7,8-dioxa-naphthalen-9-one is confirmed by their single crystal analyses.