Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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).