A Hydrazine Insertion Route to <i>N</i>′-Alkyl Benzohydrazides by an Unexpected Carbon–Carbon Bond Cleavage

Abstract

A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new <i>N</i>',<i>N</i>'-disubstituted benzohydrazides. The reaction features a regioselective formation of two carbon-nitrogen bonds and works well with a range of acrylates and hydrazines. A brief mechanistic investigation alluded to a cyclic hemiaminal as a plausible intermediate.