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Updated: Dec 1, 2025

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles
Xiao-Wei Zhang1,2, Xiao-Lin He1,2, Nan Yan1,2
1National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, China.
Abstract:
A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional groups. Control experiments support a nitrile oxide intermediate mechanism for this novel class of oxidative cyclization reactions. Moreover, synthetic applications toward bioactive molecular skeletons and the late-stage modification of drugs were realized.
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