Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intra­molecular Heck Reaction and Application towards Drug-Like Small Molecules

Abstract

A new, convenient synthesis of dibenzo[b,e]azepin-6-ones and seven-membered sultam derivatives have been envisaged via Pd-catalyzed regioselective intramolecular Heck reaction of the corresponding easily accessible precursors. This protocol has been successfully implemented to synthesize N-methyldarenzepine in four steps and in good yield. Moreover, one of the intermediates has been utilized for the synthesis of a new analogue of darenzepine. Preliminary modeling studies were performed to investigate the binding potential to muscarinic acetylcholine receptor (M4).

Key words

intramolecular Heck reaction - regioselectivity - dibenzo[b,e]azepin-6-ones - seven-membered sultams - docking - M4 receptor

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