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: i.kanizsai
avidinbiotech.com
A. Angyal, A. Demjén, J. Wölfling, L. G. Puskás, I. Kanizsai, J. Org. Chem., 2020, 85, 3587-3595.
DOI: 10.1021/acs.joc.9b03288
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Abstract
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.
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proposed mechanism
Key Words
1,3-dipolar cycloaddition, imidazoles
ID: J42-Y2020
