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KMID : 1059519950390070564
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Journal of the Korean Chemical Society
1995 Volume.39 No. 7 p.564 ~ p.571
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Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one
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Cho Nam-Sook
Park Young-Cheol
Ra Do-Young
Kang Sung-Kwon
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Abstract
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5-Amino-2H-1,2,4-thiadiazoline-3-one has been prepared from 2-thiobiuret through a oxidative cyclization under basic hydrogen peroxide condition. Lactam-lactim tautomerism of 5-amino-2H-1,2,4-thiadiazoline-3-one has been examined by spectroscopic methods and ab initio molecular orbital calculation. These results were shown that 5-amino-2H-1,2,4-thiadiazoline-3-one exists as lactam form. Reaction conditions for alkylating 5-amino-2H-1,2,4-thiadiazoline-3-one with alkyl halides in the presence of various bases were studied in DMF and H2O-THF two phase system. Li2CO3 base in DMF method gave best result in this investigation. The alkylation has been taken place at N-2 position. The identification of the product is confirmed by spectral data of IR, 1H NMR and 13C NMR and the comparison of authentic sample, 5-amino-2-methyl-1,2,4-thiadiazolidine-3-one, obtained from the oxidative cyclization of 5-methyl-2-thiobiuret.
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