Advertisement

Chemistry of Heterocyclic Compounds

, Volume 10, Issue 9, pp 1048–1052 | Cite as

Protonation of imidazo[2,1-b]thiazole and thiazolo[2,3-f]purine

  • L. M. Alekseeva
  • G. G. Dvoryantseva
  • Yu. N. Sheinker
  • I. A. Mazur
  • B. V. Kurmaz
  • P. M. Kochergin
Article
  • 53 Downloads

Abstract

The protonation of imidazo[2,1-b]thiazole and thiazolo[2,3-f]purine was investigated by PMR spectroscopy. In CF3COOH and D2SO4 the imidazothiazole forms a monocation, the structure of which corresponds to the addition of a proton to the nitrogen atom of the imidazole ring. In aqueous D2SO4 solutions, the thiazolopurine forms mono- and dications. The first protonation occurs at the nitrogen atom of the pyrimidine ring, while the second protonation occurs at the nitrogen atom of the imidazole ring. The effect of delocalization of the positive charge in the cations of the investigated compounds was examined.

Keywords

Nitrogen Spectroscopy Organic Chemistry Imidazole Nitrogen Atom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    G. G. Dvoryantseva, L. M. Alekseeva, T. N. Ul'yanova, Yu. N. Sheinker, P. M. Kochergin, and A. N. Krasovskii, Khim. Geterotsikl. Soedin., 937 (1971).Google Scholar
  2. 2.
    A. Mannschreck, W. Seitz, and H. A. Staab, Ber. Bunsenges. Phys. Chem., 67(S), 470 (1963).Google Scholar
  3. 3.
    T. Pyl, R. Jiebelman, and H. Bayer, Ann. Chem., 643, 145 (1961).Google Scholar
  4. 4.
    L. Pentimalli, G. Coga, and A. M. Guerra, Gazz. Chim. Ital., 97, 488 (1967).Google Scholar
  5. 5.
    T. Pyl, K. H. Wünsch, L. Bülling, and H. Beyer, Ann. Chem., 657, 113 (1962).Google Scholar
  6. 6.
    L. Pentimalli and A. M. Guerra, Gazz. Chim. Ital., 97, 1286 (1967).Google Scholar
  7. 7.
    L. Alimarante, L. Polo, et al., J. Med. Chem., 9, 29 (1966).Google Scholar
  8. 8.
    F. J. Bullock and O. Jardetzky, J. Org. Chem., 29, 1988 (1964).Google Scholar
  9. 9.
    S. I. Chan, M. P. Schweizer, P. O. P. Ts'o, and G. K. Helmkamp, J. Amer. Chem. Soc., 86, 4182 (1964).Google Scholar
  10. 10.
    J. M. Read and J. H. Goldstein, J. Amer. Chem. Soc., 87, 3441 (1965).Google Scholar
  11. 11.
    R. Wagner and W. Van Philipsborn, Helv. Chim. Acta, 54, 1543 (1971).Google Scholar
  12. 12.
    S. Matsuura and T. Goto, Tetrahedron Lett., 1499 (1963).Google Scholar
  13. 13.
    I. A. Mazur and P. M. Kochergin, Khim. Geterotsikl. Soedin, 508, 512 (1970).Google Scholar
  14. 14.
    M. I. Yurchenko, B. V. Kurmaz, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 996 (1972).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • L. M. Alekseeva
    • 1
    • 2
  • G. G. Dvoryantseva
    • 1
    • 2
  • Yu. N. Sheinker
    • 1
    • 2
  • I. A. Mazur
    • 1
    • 2
  • B. V. Kurmaz
    • 1
    • 2
  • P. M. Kochergin
    • 1
    • 2
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow
  2. 2.Zaporozhe State Medical InstituteUSSR

Personalised recommendations