ChemInform Abstract: Synthesis of Tetrahydro‐3‐benzazepines.

Abstract

Abstract A synthetic route toward tetrahdro-3-benzazepines 1a – f starting with 2a and 2b in modest total yield is described. The facile route was carried by Henry reaction of aldehydes 3a – e with nitroalkanes and NH 4 OAc at reflux, reduction of the resulting nitroalkenes 4a – h with LAH at rt followed by protection with K 2 CO 3 and PhSO 2 Cl at rt, one-pot oxidative cleavage annulation of olefins 5a – h with the one-pot combination of OsO 4 /NaIO 4 at reflux, and hydrogenation of the corresponding enamines 6a – f . Aldehydes 3a – e was prepared from 2a and 2b in moderate yield of three-step.