Journal
TETRAHEDRON
Volume 68, Issue 2, Pages 614-618Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.10.110
Keywords
1-Trifluoromethyl-1,3-dicarbonyl compounds; Azides; [3+2] Cycloaddition; 4-Acyl-5-trifluoromethyl-1,2,3-triazoles
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Funding
- Russian Foundation for Basic Research [10-03-00897-a, 11-03-00579-a]
- Federal Special Program [P962]
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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-5trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. (C) 2011 Elsevier Ltd. All rights reserved,
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