Thio-and Dithio-carbamates

Hamaguchi, R. Matsushita, and M. Koyama, y4 a/. Chim. Acta, 1980, 113, 

Takeshima, M. Ikeda, M. Yokoyama, N. Fukada, and M. Muraoka, J. Chem. Soc., Perkin Trans. 

Similar products are obtained from the methiodides of 2-aminopyrimidine and 

2- aminothiazole, but 4-aminopyridine methiodide gives l-methyl-4-thiopyridone. Some pyridyl-alkyl esters of dithiocarbamates have been made by treatment of the sodium salts with 2-(chloromethyl)pyridine or 2-vinylpyridine, and 6-chloro- 

3- pyridyl AW-dimethyldithiocarbamate by reaction with diazotized 3-amino-6-chloropyridine.  

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Thus, 2-thiono-5-methoxycarbonylmethylidene-4-thiazolidinones (200) and their 2-oxo-analogues (201) react with thio- and dithio-carbamates to yield the identical bicyclic adducts (202), which are autoxidized in the presence of triethylamine to the A - -bis-thiazolidin-4-ones (203). The intermediates (202) are too readily oxidized to be isolated from the reaction mixture, but they are obtainable by the reduction of (203) by zinc and acetic acid. 2-Imino-analogues of (200) react similarly. The configuration of (203) is supported by the observed displacement of their CO bands in the i.r. spectra under irradiation, similar to that of thioindigo. ... 

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