Issue 41, 2016
From the journal:

Organic & Biomolecular Chemistry

Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant†

Wei Wang,a   Hao Xu,*a   Yuanqing Xu,*a   Tao Ding,a   Wenkai Zhang,a   Yanrong Rena  and  Haibo Changa  

* Corresponding authors

a Institute of Fine Chemistry and Engineering, Henan Engineering Laboratory of Flame-retardant and Functional Materials, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China
E-mail: xuhao@henu.edu.cn, 18937822307@163.com

Abstract

A simple base-mediated one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. The reactions include three sequential procedures: base-promoted intermolecular addition of hydroxylamine to nitrile to lead to amidoxime, treatment of the amidoxime with an aldehyde to form 4,5-dihydro-1,2,4-oxadiazole, and oxidization of the 4,5-dihydro-1,2,4-oxadiazole by using another aldehyde to afford 1,2,4-oxadiazole. This method represents a direct and simple protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles.

Graphical abstract: Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant

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Article information

DOI
https://doi.org/10.1039/C6OB01794K
Article type
Paper
Submitted
17 Aug 2016
Accepted
09 Sep 2016
First published
13 Sep 2016

Org. Biomol. Chem., 2016,14, 9814-9822

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Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant

W. Wang, H. Xu, Y. Xu, T. Ding, W. Zhang, Y. Ren and H. Chang, Org. Biomol. Chem., 2016, 14, 9814 DOI: 10.1039/C6OB01794K

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