Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2<i>H</i>-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles
Anikó Angyal, András Demjén, János Wölfling, László G. Puskás, Iván Kanizsai
Abstract
-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.
Topics & Concepts
ChemistryRegioselectivityCycloadditionCatalysis1,3-Dipolar cycloadditionTrifluoroacetic acidCombinatorial chemistryNitroneOrganic chemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis