5-Nitroisoxazoles in S N Ar reactions: access to polysubstituted isoxazole derivatives

An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated. The method features excellent chemical yields, easy operability of the reaction, mild reacti...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-07, Vol.19 (29), p.6447-6454
Main Authors: Vasilenko, Dmitry A, Dronov, Sevastian E, Parfiryeu, Dzianis U, Sadovnikov, Kirill S, Sedenkova, Kseniya N, Grishin, Yuri K, Rybakov, Victor B, Kuznetsova, Tamara S, Averina, Elena B
Format: Article
Language:English
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Summary:An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated. The method features excellent chemical yields, easy operability of the reaction, mild reaction conditions and a broad scope of both 5-nitroisoxazoles and nucleophiles. A synthetic approach to 3,5- and 3,4,5-substituted isoxazoles via the sequential functionalization of the isoxazole ring has been developed based on the excellent regioselectivity of the reaction of 3,5-dinitroisoxazoles with nucleophiles.
ISSN:1477-0520
1477-0539
DOI:10.1039/D1OB00816A