An electrosynthesis of 1,3,4-oxadiazoles from N-acyl hydrazones

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Chen, Luke and Thompson, James D. F. and Jamieson, Craig (2024) An electrosynthesis of 1,3,4-oxadiazoles from N-acyl hydrazones. Chemistry - A European Journal, 30 (69). e202403128. ISSN 1521-3765 (https://doi.org/10.1002/chem.202403128)

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Abstract

The 1,3,4-oxadiazole is a widely encountered motif in the areas of pharmaceuticals, materials, and agrochemicals. This work has established a mediated electrochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from N-acyl hydrazones. Using DABCO as the optimal redox mediator has enabled a mild oxidative cyclisation, without recourse to stoichiometric oxidants. In contrast to previous methods, this indirect electrochemical oxidation has enabled a broad range of substrates to be accessed, with yields of up to 83 %, and on gram scale. The simplicity of the method has been further demonstrated by the development of a one-pot procedure, directly transforming readily available aldehydes and hydrazides into valuable heterocycles.

ORCID iDs

Chen, Luke, Thompson, James D. F. and Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272;
CORE (COnnecting REpositories)