One-pot synthesis of 1,3,4-oxadiazol-2(3H)-ones with CO2 as a C1 synthon promoted by hypoiodite

Na Yang; Gaoqing Yuan

doi:10.1039/C9OB01200A

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One-pot synthesis of 1,3,4-oxadiazol-2(3H)-ones with CO₂ as a C1 synthon promoted by hypoiodite†

Na Yang^a and Gaoqing Yuan

*^a

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* Corresponding authors

^a Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, P.R. China
E-mail: gqyuan@scut.edu.cn

Abstract

A convenient and efficient route has been developed to synthesize 1,3,4-oxadiazol-2(3H)-ones from CO₂, hydrazines and aryl or aliphatic aldehydes. Promoted by hypoiodite (IO⁻) generated in situ from KI and oxidant TBHP, the one-pot synthesis could proceed smoothly to afford the desired products in moderate to high yields. Mechanism studies revealed that nitrile imine was an important intermediate in this transformation. Notably, a commercial herbicide Oxadiazon could be successfully synthesized by this route.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01200A
Article type: Paper
Submitted: 22 May 2019
Accepted: 20 Jun 2019
First published: 21 Jun 2019

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Org. Biomol. Chem., 2019,17, 6639-6644

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One-pot synthesis of 1,3,4-oxadiazol-2(3H)-ones with CO₂ as a C1 synthon promoted by hypoiodite

N. Yang and G. Yuan, Org. Biomol. Chem., 2019, 17, 6639 DOI: 10.1039/C9OB01200A

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Organic & Biomolecular Chemistry