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A Hydrazine Insertion Route to N′‑Alkyl Benzohydrazides by an Unexpected Carbon–Carbon Bond Cleavage

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journal contribution
posted on 07.10.2019 by Ajit Kumar Jha, Rajkiran Kumari, Srinivasan Easwar
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.

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