Synthesis 2016; 48(12): 1902-1909
DOI: 10.1055/s-0035-1561597
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,2,4-Oxadiazoles via DDQ-Mediated Oxidative Cyclization of Amidoximes

Patrick D. Parker
Department of Chemistry, North Carolina State University, Raleigh NC, 27695, USA   Email: jgpierce@ncsu.edu
,
Joshua G. Pierce*
Department of Chemistry, North Carolina State University, Raleigh NC, 27695, USA   Email: jgpierce@ncsu.edu
› Author Affiliations
Further Information

Publication History

Received: 04 February 2016

Accepted after revision: 07 March 2016

Publication Date:
26 April 2016 (eFirst)

Abstract

An oxidative cyclization of amidoximes to form 1,2,4-oxadiazoles, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), is described. A range of alkyl, aryl, and heteroaryl substrates are tolerated under these conditions. This reaction serves as an alternate approach for the synthesis of functionally diverse oxadiazoles via a rapid and straightforward synthetic procedure.

Supporting Information

 
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