Synthesis and Application of Triazole Derivatives. Synthesis of 3- and 5-Acyl-1,2,4-triazoles via Lithiation of 1-Alkyl-1H-1,2,4-triazoles

Abstract

N-Unsubstituted 3-acyl-1H-l,2,4-triazoles (3), and 5-acyl-1-alkyl-1H-1,2,4-triazoles (4) were synthesized by acylation of 5-lithiotriazoles with amides. The 3-position of 1-methyl-5-phenyIthio-1H-1,2,4-triazole (11) was lithiated by lithium 2,2,6,6-tetramethylpiperidide, and acylation of the produced carbanion with amides followed by desulfurization with Raney nickel give the 3-acyl derivatives (5). The structural isomers, 3-acyl-4-alkyl-4H-1,2,4-triazoles (6), were prepared by N-methylation of 3. © 1993, The Pharmaceutical Society of Japan. All rights reserved.