P. L. Ovechkin, L. A. Ignatova, A. Gekhman
Jul 1, 1972
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Journal
Chemistry of Heterocyclic Compounds
Abstract
The reaction of 2-isothiocyano-2-methyl-4-pentanone with substituted anilines gave 4,6,6-trimethyl-3-aryl-1,2,3,6-tetrahydropyrimidine-2-thiones, which are converted to the isomeric 4,4,6-trimethyl-2-arylamino-4H-1,3-thiazines by intramolecular rearrangement by heating with hydrochloric acid. In order to study the structure and amino-imino tautomerism of the aminothiazines, their analogs with a fixed amine structure were obtained. The synthesis of model compounds was accomplished by reaction of 2-isothiocyano-2-methyl-4-pentanone with m- and p-substituted N-methylanilines and subsequent cyclization of the resulting N-methyl-N-aryl-N′-(2-methyl-4-oxo-2-amyl)thioureas to 4,4,6-trimethyl-2-methylarylamino-4H-1,3-thiazines.