Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2H-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles
- Anikó AngyalAnikó AngyalAVIDIN Ltd., Alsó kikötő sor 11/D, Szeged H-6726, HungaryDepartment of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, HungaryMore by Anikó Angyal
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- András Demjén
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- János WölflingJános WölflingDepartment of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, HungaryMore by János Wölfling
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- László G. Puskás
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- Iván Kanizsai*Iván Kanizsai*E-mail: [email protected]AVIDIN Ltd., Alsó kikötő sor 11/D, Szeged H-6726, HungaryMore by Iván Kanizsai
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.
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