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Synthesis 2018; 50(16): 3238-3242
DOI: 10.1055/s-0037-1609481
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,3,4-Oxadiazoles via Annulation of Hydrazides and Benzene-1,3,5-triyl Triformate under Metal-Free Conditions

Zhiping Yin §
a   Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany   Email: xiao-feng.wu@catalysis.de
,
Dennis J. Power §
b   School of Chemistry and Biochemistry, The University of Western Australia (M310), 35 Stirling Highway, Crawley WA 6009, Australia   Email: scott.stewart@uwa.edu.au
,
Zechao Wang
a   Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany   Email: xiao-feng.wu@catalysis.de
,
Scott G. Stewart*
b   School of Chemistry and Biochemistry, The University of Western Australia (M310), 35 Stirling Highway, Crawley WA 6009, Australia   Email: scott.stewart@uwa.edu.au
,
Xiao-Feng Wu*
a   Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany   Email: xiao-feng.wu@catalysis.de
› Author Affiliations
Further Information

Publication History

Received: 31 December 2017

Accepted after revision: 13 March 2018

Publication Date:
16 April 2018 (online)

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§ These authors contributed equally to this work.
Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

A new and efficient method for the synthesis of 1,3,4-oxadiazoles via the annulation of hydrazides with benzene-1,3,5-triyl triformate (TFBen) under metal-free conditions is reported. A broad range of hydrazides were transformed into the corresponding 1,3,4-oxadiazoles in good yields with excellent functional group tolerance.

Key words

heterocycles - cyclisation - green chemistry - carbonylation - formates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609481.
  • Supporting Information
 

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