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One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides

William S. Bechara, Inna S. Khazhieva, Elsa Rodriguez and André B. Charette*

*Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec Canada H3C 3J7, China, Email: andre.charetteumontreal.ca

W. S. Bechara, I. S. Khazhieva, E. Rodriguez, A. B. Charette, Org. Lett., 2015, 17, 1184-1187.

DOI: 10.1021/acs.orglett.5b00128 (free Supporting Information)


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Abstract

Triflic anhydride activation followed by microwave-induced cyclodehydration enables a one-pot synthesis of 3,4,5-trisubstituted 1,2,4-triazoles from secondary amides and hydrazides. In addition, the 1,2,4-triazole moiety is shown to be a useful directing group for Ru-catalyzed C-H arylation. A Pd-catalyzed intramolecular C-H functionalization reaction allows access to 1,2,4-triazolophenanthridine.

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Key Words

1,2,4-Triazoles, Microwave Synthesis


ID: J54-Y2015