Synthesis of 4-Nitroisoxazoles via NO/NO2-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones

Author:

Averina Elena B.12,Vasilenko Dmitry A.1,Sadovnikov Kirill S.1,Sedenkova Kseniya N.12,Kurova Anastasiya V.1,Grishin Yuri K.1,Kuznetsova Tamara S.1,Rybakov Victor B.1,Volkova Yulia A.13

Affiliation:

1. Department of Chemistry, Lomonosov Moscow State University

2. Institute of Physiologically Active Compounds

3. N.D. Zelinsky Institute of Organic Chemistry RAS

Abstract

A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted α,β-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t-BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.

Funder

Russian Science Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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