ol9b02657_si_001.pdf (3.7 MB)
A Hydrazine Insertion Route to N′‑Alkyl Benzohydrazides by an Unexpected Carbon–Carbon Bond Cleavage
journal contribution
posted on 2019-10-07, 19:50 authored by Ajit Kumar Jha, Rajkiran Kumari, Srinivasan EaswarA 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.