Co(II) acetateassisted direct synthesis of acyl hydrazones from acyl hydrazides under mild condition.

Abstract

Acyl hydrazones are a class of synthetically important organic compounds that are recurrently in high demand for synthesis and use in various fields of chemistry and biology. We report the first Co(II) catalyzed one-component one-pot sustainable synthesis of acyl hydrazones only from acyl hydrazides under mild reaction conditions. Traditional and contemporary methodologies use two components (usually acyl hydrazides and aldehydes/ketones/alcohols/styrene) as the coupling partners. Our protocol, on the other hand, involves the in situ generation of aldehyde intermediate (detected by gas chromatography) from the acyl hydrazide, which then undergoes condensation with another molecule of the same acyl hydrazide in the same pot to yield acyl hydrazones in presence of mild base K2CO3 and low-cost Co(OAc)2·4H2O as catalyst. This method shows good functional group tolerance with good to excellent yield of products. Furthermore, some of the resulting acyl hydrazones have been used as synthetic precursors and explored in various post-synthetic modifications to afford N-heterocyclic compounds. Furthermore, photoswitchable properties of few synthesized acyl hydrazones are also explored using their E/Z isomerization around the C=N bond, as realized by high-pressure liquid chromatography (HPLC) and UV-vis spectroscopic studies.