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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

, : 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. Chemical & Pharmaceutical Bulletin (Tokyo) 41(7): 1226-1231

N-Unsubstituted 3-acyl-1H-1,2,4-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-phenylthio-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-aklyl-4H-1,2,4-triazoles (6), were prepared by N-methylation of 3.


DOI: 10.1248/cpb.41.1226

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