Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines

Xiao-Wei Zhang*, Xiao-Lin He, Nan Yan, Hong-Xing Zheng and Xiang-Guo Hu*

*National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, China, Email: xwzhangjxnu.edu.cn, huxiangggiccas.ac.cn

X.-W. Zhang, X.-L. He, N. Yan, H.-X. Zhang, X.-G. Hu, J. Org. Chem., 2020, 85, 15726-15735.

DOI: 10.1021/acs.joc.0c02281

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Abstract

A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes providies isoxazoles or isoxazolines. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerates a variety of functional groups.

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Key Words

isoxazoles, isoxazolines, TBN

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ID: J42-Y2020