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Note | Regular issue | Vol 60, No. 6, 2003, pp.1401-1409
Published online, 7th April, 2003
DOI: 10.3987/COM-03-9742
Oxidative Cyclization of Dithiobiuret under Basic Condition and Theoretical Tautomeric Studies of 5-Amino-2,3-dihydro-1,2,4-thiadiazole-3-thione

Nam Sook Cho,* Young Hoon Kim, Mi Sun Park, Eun Hee Kim, Sung Kwon Kang, and Chang-moon Park

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

Abstract

The oxidative cyclization of dithiobiuret under basic conditions (NaOH-H2O2 or CH3CO3H) afforded bis(5-amino-1,2,4-thiadiazolyl) 3,3’-disulfide (5), oxidative dimer form of 5-amino-3-mercapto-1,2,4-thiadiazole (3b). The theoretical tautomeric study (ab initio calculations) shows that the most stable tautomeric form of 3 is 5-amino-3-mercapto-1,2,4-thiadiazole (3b) among the four possible tautomers. Thus, 3b is speculated as an intermediate of the formation of the compound (5).