One-pot synthesis and hydrokylaminolysis of asymmetrical acyclic nitrones

Abstract

Aromatic aldehydes were reductively aminated to the corresponding secondary amines using NaBH4 in methanol in good yields. Amines were oxidized with H2O2-WO42- regioselectively to nitrones, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes and benzyl or methyl hydroxylamine hydrochlorides.