A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes

Wei Guo; Kunbo Huang; Fanghua Ji; Wanqing Wu; Huanfeng Jiang

doi:10.1039/C5CC02110C

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A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes†

Wei Guo,^ab Kunbo Huang,^a Fanghua Ji,^a Wanqing Wu^a and Huanfeng Jiang*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
E-mail: jianghf@scut.edu.cn
Fax: +86-20-87112906
Tel: +86-20-87112906

^b Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou, China

Abstract

Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation–amination–cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.

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Article information

DOI: https://doi.org/10.1039/C5CC02110C
Article type: Communication
Submitted: 12 Mar 2015
Accepted: 14 Apr 2015
First published: 14 Apr 2015

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Chem. Commun., 2015,51, 8857-8860

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A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes

W. Guo, K. Huang, F. Ji, W. Wu and H. Jiang, Chem. Commun., 2015, 51, 8857 DOI: 10.1039/C5CC02110C

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Chemical Communications

A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes†

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A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes

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