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

The first 1,3-dipolar cycloaddition of 2 -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...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3587-3595
Main Authors: Angyal, Anikó, Demjén, András, Wölfling, János, Puskás, László G, Kanizsai, Iván
Format: Article
Language:English
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Summary:The first 1,3-dipolar cycloaddition of 2 -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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03288