Abstract
Substituted 4-hydroxyhexahydropyrimidine-2-thiones were obtained by the reaction of β-isothiocyanatoaldehydes with ammonia or methylamine. When heated with alcohols in the presence of p-toluenesulfonic acids, the synthesized compounds gave the corresponding 4-alkoxyhexahydropyrimidine-2-thiones, which were converted into other 4-alkoxy derivatives by the action of the respective alcohols and were hydrolyzed to the initial 4-hydroxyhexahydropyrimidine-2-thiones by the action of an aqueous solution of oxalic acid or potassium hydroxide. The reaction of the 4-hydroxyhexahydropyrimidine-2-thiones with methyl iodide led to the formation of 2-methylthio-4-hydroxy-3,4,5,6-tetrahydropyrimidine hydriodides. It was shown by PMR spectroscopy that the stereoisomers in which the hydroxyl (or alkoxyl) group has the axial orientation are thermodynamically more stable.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 260–266, February, 1985.
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Ignatova, L.A., Shutalev, A.D., Shingareeva, A.G. et al. Reactivity and stereochemical structure of 4-hydroxy- and 4-alkoxyhexahydropyrimidine-2-thiones. Chem Heterocycl Compd 21, 218–224 (1985). https://doi.org/10.1007/BF00504213
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DOI: https://doi.org/10.1007/BF00504213