Advertisement

Chemistry of Heterocyclic Compounds

, Volume 48, Issue 8, pp 1220–1227 | Cite as

Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  • R. A. Gazzaeva
  • E. V. Trofimova
  • A. Z. Kadzhaeva
  • A. N. Fedotov
  • S. S. Mochalov
Article

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system.

Keywords

benzylcyclopropanes benzyl-4,5-dihydroisoxazoles nitrous acid heterocyclization induced by the nitrosyl cation nitrosylation SET mechanism 

References

  1. 1.
    S. S. Mochalov, Ya. I. Kuz’min, A. N. Fedotov, E. V. Trofimova, R. A. Gazzaeva, Yu. S. Shabarov, and N. S. Zefirov, Zh. Org. Khim., 34, 1379 (1998).Google Scholar
  2. 2.
    S. S. Mochalov, R. A. Gazzaeva, A. N. Fedotov, E. V. Trofimova, I. V. Trushkov, and N. S. Zefirov, Zh. Org. Khim., 40, 1146 (2004).Google Scholar
  3. 3.
    M. M. Smirnova, A. V. Geiderikh, S. S. Mochalov, and Yu. S. Shabarov, Zh. Org. Khim., 24, 1189 (1988).Google Scholar
  4. 4.
    A. A. Samodov, S. S. Mochalov, and I. Y. Shchapin, in: International Conference on Reaction Mechanisms and Organic Intermediates. Book of Abstracts, June 11-14, St. Petersburg, Russia (2001), p. 137.Google Scholar
  5. 5.
    Yu. S. Shabarov, L. G. Saginova, and R. A. Gazzaeva, Khim. Geterotsikl. Soedin., 738 (1983). [Chem. Heterocycl. Compd., 19, 589 (1983)].CrossRefGoogle Scholar
  6. 6.
    R. A. Gazzaeva, Yu. S. Shabarov, and L. G. Saginova, Khim. Geterotsikl. Soedin., 309 (1984). [Chem. Heterocycl. Compd., 20, 246 (1984)].CrossRefGoogle Scholar
  7. 7.
    Yu. S. Shabarov, L. G. Saginova, and R. A. Gazzaeva, Khim. Geterotsikl. Soedin., 738 (1983). [Chem. Heterocycl. Compd., 19, 589 (1983)].CrossRefGoogle Scholar
  8. 8.
    A. Z. Kadzhaeva, E. V. Trofimova, A. N. Fedotov, K. A. Potekhin, R. A. Gazzaeva, S. S. Mochalov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 753 (2009). [Chem. Heterocycl. Compd., 45, 595 (2009)].CrossRefGoogle Scholar
  9. 9.
    S. S. Mochalov, R. A. Gazzaeva, A. Z. Kadzhaeva, A. N. Fedotov, and E. V. Trofimova, Khim. Geterotsikl. Soedin., 1702 (2011). [Chem. Heterocycl. Compd., 47, 1415 (2011)].CrossRefGoogle Scholar
  10. 10.
    R. A. Gazzaeva, S. S. Mochalov, B. P. Archegov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 302 (2005). [Chem. Heterocycl. Compd., 41, 272 (2005)].CrossRefGoogle Scholar
  11. 11.
    A. N. Fedotov, E. V. Trofimova, S. S. Mochalov, and Yu. S. Shabarov, Zh. Org. Khim., 24, 1413 (1988).Google Scholar
  12. 12.
    S. Uemura, A. Toshimitsu, and M. Okano, J. Chem. Soc., Perkin Trans. 1, 1076 (1978).Google Scholar
  13. 13.
    T. Clark, A Handbook of Computational Chemistry, Wiley, New York (1985).Google Scholar
  14. 14.
    K. Mizuno, N. Ichinose, T. Tamai, and Y. Otsuji, J. Org. Chem., 57, 4669 (1992).CrossRefGoogle Scholar
  15. 15.
    E. V. Trofimova, B. P. Archegov, A. N. Fedotov, R. A. Gazzaeva, S. S. Mochalov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 1368 (2009). [Chem. Heterocycl. Compd., 45, 1095 (2009)].CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  1. 1.K. L. Khetagurov North-Ossetian State UniversityVladikavkazRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia

Personalised recommendations