Advertisement

Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 709–716 | Cite as

Halocyclization of products of allyl isothiocyanate addition to acyclic methylene active compounds

  • M. B. Litvinchuk
  • A. V. Bentya
  • N. Yu. Slyvka
  • M. V. Vovk
Article

Abstract

Products of allyl isothiocyanate addition to methylene active compounds, salt-like N-allyl-N,S-ketenacetals or N-allylthioamides, react with iodine, bromine or N-bromosuccinimide with the formation of derivatives of 2-ylidene-5-halomethylthiazolidines. A dependence was found of isomeric composition of obtained thiazolidines on the solvent nature.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Zankowska-Jasinska, W., Burgiel, M., Danel, A., and Sygula, A., J. Prakt. Chem., 1988, vol. 330, p. 795. doi 10.1002/prac.19883300516CrossRefGoogle Scholar
  2. 2.
    Bernát, J., Chomca, I., Kristian, P., Pihlaja, K., and Klika, K.D., Heterocycles, 1999, vol. 51, p. 137. doi 10.3987/COM-98-8308CrossRefGoogle Scholar
  3. 3.
    El-Taweel, F.M.A., Phosph., Sulfur, Silicon, Relat. Elem., 2004, vol. 179, p. 1267. doi 10.1080/10426500490468083CrossRefGoogle Scholar
  4. 4.
    Basheer, A. and Rappoport, Z., J. Org. Chem., 2006, vol. 71, p. 9743. doi 10.1021/jo061835gCrossRefGoogle Scholar
  5. 5.
    Shishoo, C.J., Devani, M.B., Ananthan, S., Bhadti, V.S., and Ullas, G.V., J. Heterocycl. Chem., 1988, vol. 25, p. 759. doi 10.1002/jhet.5570250311CrossRefGoogle Scholar
  6. 6.
    Varaprasad, C.V.N.S., Barawkar, D., El Abdellaoui, H., Chakravarty, S., Allan, M., Chen, H., Zhang, W., Wu, J.Z., Tam, R., Hamatake, R., Lang, S., and Hong, Z., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 3975. doi 10.1016/j.bmcl.2006.05.019CrossRefGoogle Scholar
  7. 7.
    El Abdellaoui, H., Varaprasad, C.V.N.S., Barawkar, D., Chakravarty, S., Maderna, A., Tam, R., Chen, H., Allan, M., Wu, J.Z., Appleby, T., Yan, S., Zhang, W., Lang, S., Yao, N., Hamatake, R., and Hong, Z., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5561. doi 10.1016/j.bmcl.2006.08.048CrossRefGoogle Scholar
  8. 8.
    Yan, S., Appleby, T., Gunic, E., Shim, J.H., Tasu, T., Kim, H., Rong, F., Chen, H., Hamatake, R., Wu, J.Z., Hong, Z., and Yao, N., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 28. doi 10.1016/j.bmcl.2006.10.002CrossRefGoogle Scholar
  9. 9.
    Larson, G., Yan, S., Chen, H., Rong, F., Hong, Z., and Wu, J.Z., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 172. doi 10.1016/j.bmcl.2006.09.067CrossRefGoogle Scholar
  10. 10.
    Sommen, G., Comel, A., and Kirsch, G., Tetrahedron, 2003, vol. 59, p. 1557. doi 10.1016/S0040-4020(03)00054-1CrossRefGoogle Scholar
  11. 11.
    Bernát, J., Kristian, P., Guspanová, J., and Chomca, I., Heterocycles, 2000, vol. 53, p. 1171. doi 10.3987/COM-00-8845CrossRefGoogle Scholar
  12. 12.
    Zhou, W., Ni, S., Mei, H., Han, J., and Pan, Y., Tetrahedron Lett., 2015, vol. 56, p. 4128.CrossRefGoogle Scholar
  13. 13.
    Minakata, S., Morino, Y., Oderatoshi, Y., and Komatsu, M., Org. Lett., 2006, vol. 8, p. 3335. doi 10.1021/ol061182qCrossRefGoogle Scholar
  14. 14.
    Worrall, D.E., J. Am. Chem. Soc., 1932, vol. 54, p. 2061.CrossRefGoogle Scholar
  15. 15.
    Just, G. and Rossy, P., J. Org. Chem., 1972, vol. 37, p. 318. doi 10.1021/jo00967a031CrossRefGoogle Scholar
  16. 16.
    Wesolowska, A., Jagodzinski, T.S., Sosnicki, J.G., and Hansen, P.E., Polish J. Chem., 2001, vol. 75, p. 387.Google Scholar
  17. 17.
    Nishio, T., Helv. Chim. Acta, 1998, vol. 81, p. 1207. doi 10.1002/hlca.19980810531CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • M. B. Litvinchuk
    • 1
  • A. V. Bentya
    • 2
  • N. Yu. Slyvka
    • 1
  • M. V. Vovk
    • 2
  1. 1.Lesya Ukrainka Eastern-European National UniversityLutskUkraine
  2. 2.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

Personalised recommendations