Organic Chemistry Portal



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

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

*AVIDIN Ltd., Alsó kikötő sor 11/D, Szeged H-6726, Hungary, Email:

A. Angyal, A. Demjén, J. Wölfling, L. G. Puskás, I. Kanizsai, J. Org. Chem., 2020, 85, 3587-3595.

DOI: 10.1021/acs.joc.9b03288

see article for more reactions


A regioselective 1,3-dipolar cycloaddition of 2H-azirines with nitrones provides 1,2,4,5-tetrasubstituted imidazoles in the presence of trifluoroacetic acid as catalyst. The mild protocol tolerates a broad range of aliphatic and aromatic substrates, and offers an efficient access to highly diverse, multisubstituted imidazoles in very good isolated yields.

see article for more examples

proposed mechanism

Key Words

1,3-dipolar cycloaddition, imidazoles

ID: J42-Y2020