Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF 3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides

Abstract

1-Trifluoromethyl-substituted 1,3-dicarbonyl compounds are shown to undergo 100% regioselective cyclization in reactions with alkyl and aryl azides to form 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The reaction represents a general method for the synthesis of otherwise difficulty available 4-acyl-5- trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. © 2011 Elsevier Ltd. All rights reserved.