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Report | Regular issue | Vol 23, No. 9, 1985, pp.2371-2374
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2371
New Methods and Reagents in Organic Synthesis. 54. Lithium Trimethylsilylydiazomethane: A New Synthon for the Preparation of 1-Substituted 5-Alkylthio-1,2,3-triazoles from Isothiocyanates

Toyohiko Aoyama,* Mototsugu Kabeya, and Takayuki Shioiri

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

Lithium trimethylsilyldiazomethane (1) reacts smoothly with isothiocyanates in tetrahydrofuran to give 1-substituted 4-trimethylsilyl-5-alkylthio-1,2,3-triazoles (2) after quenching with alkyl halides. Desilylation of 2 is easily achieved with 10% aqueous potassium hydroxide in methanol to afford 1-substituted 5-alkylthio-1,2,3-triazoles (3).