A Hydrazine Insertion Route to N'-Alkyl Benzohydrazides by an Unexpected Carbon-Carbon Bond Cleavage

Org Lett. 2019 Oct 18;21(20):8191-8195. doi: 10.1021/acs.orglett.9b02657. Epub 2019 Oct 7.

Abstract

A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new N',N'-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.