Summary
6-Amino-thiazolo[4,5-c]isothiazole derivatives4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile2 followed by cyclooxidation of the intermediate thioamides3. In the presence of sodium sulfite the hydrolysis of the4-amino-2-methylthio-thiazolium salts5 derived from the title compounds1 yields the4-amino-thiazolin-2-ones6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols15a–h and13i–e. They have been isolated as their disulfides14 or 5-alkyl derivativesi.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione24 derived from1 react by ring cleveage to yield the 1,4-and 4,6-diamino-pyrimidin-5-thiole derivatives22 and27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine16b the pyrimido[5,4-b]1,4-thiazine derivative18 can be obtained.
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Literatur
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Gewald, K., Hain, U., Schindler, R. et al. Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.. Monatsh Chem 125, 1129–1143 (1994). https://doi.org/10.1007/BF00811521
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DOI: https://doi.org/10.1007/BF00811521