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

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journal contribution
posted on 17.02.2020, 20:37 by Anikó Angyal, András Demjén, János Wölfling, László G. Puskás, Iván Kanizsai
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.