Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2 H-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles

Anikó Angyal, András Demjén, János Wölfling, László G. Puskás, Iván Kanizsai

Research output: Contribution to journalArticle

Abstract

The first 1,3-dipolar cycloaddition of 2H-azirines with nitrones, a straightforward approach toward the regioselective synthesis of 1,2,4,5-tetrasubstituted imidazoles, is reported. This trifluoroacetic acid-catalyzed protocol tolerates a broad range of aliphatic and aromatic substrates, offering an efficient access to highly diverse, multisubstituted imidazoles in isolated yields up to 83% under mild conditions.

Original languageEnglish
Pages (from-to)3587-3595
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number5
DOIs
Publication statusPublished - Mar 6 2020

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ASJC Scopus subject areas

  • Organic Chemistry

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