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Note | Regular issue | Vol 55, No. 3, 2001, pp.579-587
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9147
Regiospecific Alkylation of 5-Substituted 2-Acylamino-1,3,4-thiadiazoles

Nam Sook Cho,* Hye Jeong Hwang, Jin-Gyu Kim, and Il-Hwan Suh

*Department of Chemistry, College of Natural Sciences, Chungnam National University, Taejon 305-764, Korea

Abstract

5-Substituted 2-acylamino-1,3,4-thiadiazoles (2 and 3b) are quantitatively and regiospecifically alkylated with alkyl bromide at the 3-position nitrogen (endo-products) rather than at the 2-position amide-nitrogen (exo-products) under basic conditions. This alkylation required more than 1.5 equivalents of base and more than four equivalents of alkyl bromide. The structures of the products, 5-substituted 2-acylimino-3-alkyl-1,3,4-thiadiazolines (4 and 5b2), were clearly established by spectroscopic data. Especially, the structure of 3-ethyl-5-ethylthio-2-p-toluoylimino-1,3,4-thiadiazoline (4d1) was proven by X-Ray crystallography.