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Note | Regular issue | Vol 57, No. 10, 2002, pp.1919-1933
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9558
Synthesis of Heteromacrocycles Containing 2-Imino-5-mercapto-2,3-dihydro-1,3,4-thiadiazoles as a Subunit

Nam Sook Cho,* Jin Gap Oh, Hye Jeong Hwang, Jin-Guy Kim, and Il-hwan Suh

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

Abstract

Macrocycles containing two 2-imino-5-mercapto-2,3-dihydro-1,3,4-thiadiazole subunits linked to the 3- and 5-positions of the heterocycle unit were prepared by regiospecific alkylation of 5-amino-2,3-dihydro-1,3,4-thiadizole-2-thione and 2-acetylamino-5-alkylthio-1,3,4-thiadizoles, respectively. The structures of the macrocycles were established from 1H and 13C NMR, IR, MS spectrometries and elemental analyses. Moreover, the structure of the macrocycle 1,5-[5,5’-(1,3-phenylenedimethylenedithio)bis(2,3-dihydro-2-acetylimino-1,3,4-thiadiazol-2-yl)]-3-oxapentane (4b) was supported by X-Ray crystallography.