Assembly of N-Heterocyclic Carbenes and Nitroalkenes for Access to Isoxazole Derivatives

Organic Letters 2026

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Authors: Zhiguo Zheng, Ali Dai, Jian Wu, Shengxin Guo, Ge‐Fei Hao, Linhong Jin, Barana Chaminda Jayawardana, B. Marambe, Shiqing Huang, Zonglin Liu, Zhichao Jin
DOI: 10.1021/acs.orglett.6c01097
Cited by: 1
References: 48

Abstract

A direct isoxazole synthesis employing N-heterocyclic carbenes (NHCs) as single-carbon synthons is reported. Using imidazolium salts as carbon donors, nitroalkenes are transformed into 5-amino-substituted isoxazoles via a nucleophilic addition-cycloaddition-ring opening-hydrolysis cascade reaction. This mild process simultaneously constructs C-O and C-C bonds, accessing products that are difficult to obtain by classical methods. The proposed reaction mechanism is supported by both experimental and computational studies. Several derivatives exhibit broad-spectrum antifungal activity, highlighting their potential as fungicide leads.

Fields of Study & Subjects

N-Heterocyclic Carbenes in Organic and Inorganic Chemistry Cyclopropane Reaction Mechanisms Quinazolinone synthesis and applications

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
16
Pages
5218–5223
Publication date
11 April 2026
Language
EN