Chemistry of Heterocyclic Compounds

, Volume 23, Issue 10, pp 1105–1112 | Cite as

Cyclization reactions of nitriles. 26. Synthesis, structure, and properties of 2-amino-4-methylthio-5-cyano-6(1H)-pyrimidinethione

  • Yu. A. Sharanin
  • A. M. Shestopalov
  • V. N. Nesterov
  • V. P. Litvinov
  • V. Yu. Mortikov
  • V. K. Promonenkov
  • V. E. Shklover
  • Yu. T. Struchkov
Article

Abstract

2-Amino-4-methylthio-5-cyano-6(1H)-pyrimidinethione has been prepared via treatment of N-cyanodimethyldithioimidate or 1,1-di(methylthio)-2-thiocar-bamoyl-2-cyanoethylene with cyanothioacetamide or cyanamide. The structure of the complex formed between 2-amino-4-methylthio-5-cyano-6(1H)-pyrimidinethione and urea has been studied by x-ray structural analysis. Thieno[2,3-d]pyrimidines and thiazolo[3,2-c]pyrimidinium salts have been synthesized based on the 6(1H)-pyrimidinethione.

Keywords

Urea Organic Chemistry Nitrile Structural Analysis Pyrimidine 

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Literature Cited

  1. 1.
    Yu. A. Sharanin, A. M. Shestopalov, V. P. Litvinov, G. V. Klokol, V. Yu. Mortikov, and A. S. Demerkov, Zh. Org. Khim., in press.Google Scholar
  2. 2.
    S. Rajappa and R. Sreenivasan, Indian J. Chem., 9, 761 (1971).Google Scholar
  3. 3.
    J. L. Soto, A. Loreute, N. Garcia, and L. Jose, An. Quim., C77, 255 (1981).Google Scholar
  4. 4.
    M. A. Perez, J. L. Soto, and J. R. Carrillo, Synthesis, No. 5, 402 (1983).Google Scholar
  5. 5.
    F. J. Cuadrado, M. A. Perez, and J. L. Soto, J. Chem. Soc., Perkin Trans. I, No. 10, 2447 (1984).Google Scholar
  6. 6.
    A. A. Krauze, é. é. Liepin'sh, Yu. é. Pelcher, Z. A. Kalme, I. V. Dipan, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 1, 95 (1985).Google Scholar
  7. 7.
    V. P. Litvinov, V. K. Promonenkov, Yu. A. Sharanin, A. M. Shestopalov, L. A. Rodinovskaya, V. Yu. Mortikov, and V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2101 (1985).Google Scholar
  8. 8.
    V. N. Nesterov, V. E. Shklover, Yu. T. Struchkov, Yu. A. Sharanin, A. M. Shestopalov, and L. A. Rodinovskaya, Acta Crystallogr., C41, 1191 (1985).Google Scholar
  9. 9.
    International Tables for X-Ray Crystallography, Kynoch Press, Birmingham (1968), Vol. 3, p. 276.Google Scholar
  10. 10.
    M. Burke-Laing and M. Laing, Acta Crystallogr., B32, 3216 (1976).Google Scholar
  11. 11.
    A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York (1973), p. 431.Google Scholar
  12. 12.
    S. Furberg, J. Grogaard, and B. Smedsrud, Acta Chem. Scand., B33, 715 (1979).Google Scholar
  13. 13.
    J. Scheinbein and E. Schempp, Acta Crystallogr., B32, 607 (1976).Google Scholar
  14. 14.
    H. W. Kroto and B. M. Landsberg, J. Mol. Spectrosc., 62, 346 (1976).Google Scholar
  15. 15.
    M. Gadret, M. Goursolle, and J. M. Leger, Acta Crystallogr., B30, 1598 (1974).Google Scholar
  16. 16.
    Gy. Argay, A. Kàlmàn, A. Nahlovski, and B. Ribàr, Acta Crystallogr., B31, 1956 (1975).Google Scholar
  17. 17.
    G. Pepe and M. Pierrot, Acta Crystallogr., B32, 1321 (1976).Google Scholar
  18. 18.
    D. Mullen and E. Hellner, Acta Crystallogr., B34, 1624 (1978).Google Scholar
  19. 19.
    A. Bondi, J. Phys. Chem., 70, 3006 (1966).Google Scholar
  20. 20.
    N. Walker and D. Stuart, Acta Crystallogr., A39, 158 (1983).Google Scholar
  21. 21.
    R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya, 28, 1029 (1983).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • Yu. A. Sharanin
    • 1
    • 2
    • 3
  • A. M. Shestopalov
    • 1
    • 2
    • 3
  • V. N. Nesterov
    • 1
    • 2
    • 3
  • V. P. Litvinov
    • 1
    • 2
    • 3
  • V. Yu. Mortikov
    • 1
    • 2
    • 3
  • V. K. Promonenkov
    • 1
    • 2
    • 3
  • V. E. Shklover
    • 1
    • 2
    • 3
  • Yu. T. Struchkov
    • 1
    • 2
    • 3
  1. 1.T. G. Shevchenko Voroshilovgrad State Pedagogical InstituteVoroshilovgrad
  2. 2.N. D. Zelinskii, Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow
  3. 3.A. N. Nesmeyanov Institute of Organometallic ChemistryAcademy of Sciences of the USSRMoscow

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