Chemistry of Heterocyclic Compounds

, Volume 7, Issue 1, pp 70–73 | Cite as

Nitrogen- and sulfur-containing heterocycles

XIX. 7H-4-chloro-6-aryl- and 5H-pyrimido[4,5-b][1,4]thiazines
  • M. P. Nemeryuk
  • T. S. Safonova


4-Chloro-5-amino- and 4-chloro-5-methylamino-6-phenacylmercaptopyrimidines (II–V and XVI–XX) were obtained by the reaction of 4-chloro-5-amino- and 4-chloro-5-methylamino-6-mercaptopyrimidines (I and XV) with phenacyl halides. It is shown that II–V are cyclized by alkalis to 4-chloro-6-aryl-6-hydroxy-5,6-dihydropyrimido[4,5-b][1,4]thiazines (VI–IXa), while both II–IXa and XVI–XIX, respectively, are converted to 7H-4-chloro-6-aryl- (X–XIII) and 5H-4-chloro-5-methyl-6-arylpyrimido[4,5-b][1,4]thiazines (XX–XXIII) under the influence of acidic reagents.


Nitrogen Organic Chemistry Halide Acidic Reagent Phenacyl 
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Literature cited

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    M. P. Nemeryuk and T. S. Safonova, Khim. Geterotsikl. Soedin., 486 (1967),Google Scholar
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    T. S. Safonova and M. P. Nemeryuk, Khim. Geterotsikl. Soedin., 735 (1968).Google Scholar
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    U. R. Jenks, Current Problems in Physical Organic Chemistry [Russian translation], Moscow (1967), p. 342.Google Scholar
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    C. Temple, R. J. McKee, and I. A. Montgomery, J. Org. Chem., 28, 923 (1963).Google Scholar
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    T. S. Safonova and L. G. Levkovskaya, Khim. Geterotsikl. Soedin., 68 (1971).Google Scholar

Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • M. P. Nemeryuk
    • 1
  • T. S. Safonova
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Re search Pharmaceutical-Chemistry InstituteMoscow

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