Mechanochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Mediated by PPh₃-TCCA

Dolnapa Yamano, Nittaya Wiriya, Wong Phakhodee, Sirawit Wet-osot, Mookda Pattarawarapan*

*Department of Chemistry, Faculty of Science, Chiang Mai, University, Chiang Mai 50200, Thailand, Email: mookdap55gmail.com

D. Yamano, N. Wiriya, W. Phakhodee, S. Wet-osot, M. Pattarawarapan, Synlett, 2022, 33, 1458-1462.

DOI: 10.1055/s-0040-1719867

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Abstract

A mechanochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles is an environmentally benign alternative to conventional solvent-based methods. In the presence of triphenylphosphine and trichloroisocyanuric acid, N-acylbenzotriazoles condense with acylhydrazides to provide oxadiazoles derivatives in very good yields within minutes. A range of reactive functionalities was well tolerated.

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Key Words

N-acylbenzotriazoles, liquid-assisted grinding, mechanochemistry, 1,3,4-oxadiazoles, triphenylphosphine, trichloroisocyanuric acid

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ID: J72-Y2022