Heterocyclic thiones and their analogs in 1,3-dipolar cycloaddition: VII. Reaction of 4-methyl-1,3-thiazole-2(3H)-thiones with nitrile imines

  • E. V. Budarina
  • T. S. Dolgushina
  • M. L. Petrov
  • N. N. Labeish
  • A. A. Kol’tsov
  • V. K. Bel’skii
Article

Abstract

Reactions of 4-methyl-1,3-thiazole-2(3H)-thiones with various C,N-disubstituted nitrile imines occurred by the common [3+2]-cycloaddition scheme leading to the formation in general of stable spiro compounds. In reactions of o-nitrophenylnitrile imines acyclic compounds were the main products.

References

  1. 1.
    Firsova, O.V., Dolgushina, T.S., Polukeev, V.A., Ioannisyan, E.M., Zavodnik, V.E., Stash, A.I., Bel’skii, V.K., and Galishev, V.A., Zh. Org. Khim., 2005, vol. 41, p. 776.Google Scholar
  2. 2.
    Huisgen, R., Grashey, R., Seidel, M., Knupfer, H., and Schmidt, R., Lieb. Ann., 1962, vol. 658, p. 169.CrossRefGoogle Scholar
  3. 3.
    1,3-Dipolar Cycloaddition Chemistry, Padwa, A. and Wiley, J., Eds., New York: J. Wiley & Sons, 1984, vol. 1, p. 360.Google Scholar
  4. 4.
    Labeish, N.N., Oparin, D.A., Bel’skii, V.K., and Galishev, V.A., Zh. Org. Khim., 1997, vol. 33, p. 1100.Google Scholar
  5. 5.
    Abbass, I.M., Abdallah, M.A., Mosselhi, M.A.N., Mohamed, S.Z., and Shawali, A.S., J. Chem. Res. Synop., 1994, p. 308.Google Scholar
  6. 6.
    Abdallah, M.A., Mosselhi, M.A.N., Abbas, I.M., Fahmi, A.-G.A., and Shawali, A.S., J. Chem. Res. Synop., 1995, p. 370.Google Scholar
  7. 7.
    Mosselhi, M.A.N., Abdallah, M.A., Abbas, I.M., Mohamed, S.Z., and Shawali, A.S., J. Chem. Res. Synop., 1995, p. 646.Google Scholar
  8. 8.
    Firsova, O.V., Dolgushina, T.S., Polukeev, V.A., Zavodnik, V.E., Stash, A.I., Bel’skii, V.K., and Galishev, V.A., Zh. Org. Khim., 2004, vol. 40, 1059.Google Scholar
  9. 9.
    Firsova, O.V., Dolgushina, T.S., Polukeev, V.A., Zavodnik, V.E., Stash, A.I., Bel’skii, V.K., and Galishev, V.A., Zh. Org. Khim., 2004, vol. 40, 1222.Google Scholar
  10. 10.
    Budarina, E.V., Dolgushina, T.S., Petrov, M.L., Labeish, N.N., Kol’tsov, A.A., and Bel’skii, V.K., Zh. Org. Khim., 2005, vol. 41, p. 315.Google Scholar
  11. 11.
    Rakib, E.M., Benchidmi, M., Essassi, E.M., Bouadili, A.E., Khouili, M., Barbe, J.M., and Pujol, M.D., Heterocycles, 2000, vol. 53, p. 571.CrossRefGoogle Scholar
  12. 12.
    Dovlatyan, V.V., Eliazyan, K.A., Pivazyan, V.A., Kazaryan, E.A., Engoyan, A.P., Grigoryan, R.T., and Mirzoyan, R.G., Khim. Geterotsikl. Soedin., 2000, p. 677.Google Scholar
  13. 13.
    Huisgen, R., Seidel, M., Wallbilich, G., and Knupfer, H., Tetrahedron, 1962, vol. 17, no. 1, p. 3.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • E. V. Budarina
    • 1
  • T. S. Dolgushina
    • 1
  • M. L. Petrov
    • 1
  • N. N. Labeish
    • 1
  • A. A. Kol’tsov
    • 1
  • V. K. Bel’skii
    • 2
  1. 1.St. Petersburg State Technological InstituteSt. PetersburgRussia
  2. 2.State Scientific Center Karpov Research Physicochemical InstituteMoscowRussia

Personalised recommendations