Skip to main content
SpringerLink
Log in

New scheme of the mechanism of Fischer indolization

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An expanded and fundamentally new scheme of the mechanism of Fischer indolization has been constructed on the basis of quantum chemical calculations of the energetic, electronic, and structural indices, as well as a study of the regioselectivity, kinetic and spectrometric characteristics of some phenylhydrazones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. M. Robinson and R. Robinson, J. Chem. Soc., No. 125, 1734 (1924).

  2. C. F. H. Allen and C. V. Wilson, J. Am. Chem. Soc.,65, No. 4, 611 (1943).

    Google Scholar 

  3. N. Pleninger and J. Nogradi, Chem. Ber.,88, 1964 (1955).

    Google Scholar 

  4. A. M. Douglas, J. Am. Chem. Soc.,101, 5676 (1979).

    Google Scholar 

  5. K. Clusius and H. R. Weiser, Helv. Chim. Acta,35, 400 (1952).

    Google Scholar 

  6. N. N. Suvorov, N. P. Sorokina, and Yu. N. Sheinker, Zh. Obshch. Khim.,28, 1090 (1958).

    Google Scholar 

  7. B. I. Geller, Uspekhi Khim., No. 3, 537 (1978).

  8. K. H. Pousacker and C. Y. Schubert, Nature,163, 289 (1949).

    Google Scholar 

  9. P. H. Gore, C. K. Hughes, and H. Ritchie, Nature,164, 835 (1949).

    PubMed  Google Scholar 

  10. A. E. Arbuzov and Yu. P. Kitaev, Transactions of the Kazan' Chemico-technological Institute [in Russian], No. 23 (1957), p. 60.

  11. A. E. Arbuzov and Yu. P. Kitaev, Zh. Obshch. Khim.,27, 2328 (1957).

    Google Scholar 

  12. I. I. Grandberg and V. I. Sorokin, Uspekhi Khim.,43, 266 (1974).

    Google Scholar 

  13. I. I. Grandberg, Izv. TSKhA, No. 5, 188 (1972).

  14. N. M. Przheval'skii, I. I. Grandberg, and N. A. Klyuev, Khim. Geterotsikl. Soed., No. 8, 1065 (1976).

  15. V. A. Zagorevskii, N. F. Kucherova, N. N. Sharkova, T. I. Ivanova, and S. I. Klyuev, Khim. Geterotsikl. Soedin., No. 10, 1353 (1975).

  16. M. A. Tsikoliya, Dzh. Kereselidze, and Sh. A. Samsoniya, Soobshch. Akad. Nauk Gruzii,147, 408 (1993).

    Google Scholar 

  17. Dzh. A. Kereselidze, Zh. Fiz. Khim., No. 7, 1534 (1993).

  18. Dzh. A. Kereselidze, Izv. RAN Ser. Khim., No. 5, 961 (1994).

  19. Dzh. A. Kereselidze, N. I. Raevskii, Sh. A. Samsoniya, I. Sh. Chikvaidze, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 8, 1038 (1991).

  20. Dzh. A. Kereselidze, N. I. Raevskii, and Yu. A. Borisov, Izv. RAN Ser. Khim., No. 1, 220 (1993).

  21. Dzh. A. Kereselidze, Sh. A. Samsoniya, I. Sh. Chikvaidze, M. A. Tsikoliya, and N. P. Suvorov, ZhOrKh.,27, 1365 (1991).

    Google Scholar 

  22. Dzh. A. Kereselidze, Sh. A. Samsoniya, and M. A. Tsikoliya, Soobshch. Akad. Nauk Gruzii,143, 411 (1991).

    Google Scholar 

  23. A. A. Stolov, M. D. Borisover, B. I. Solomonov, D. I. Kashalova, S. V. Izosimova, and M. S. Pominov, Zh. Fiz. Khim.,66, No. 3, 620 (1992).

    Google Scholar 

  24. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. P. Stewart, J. Am. Chem. Soc.,107, No. 13, 3902 (1985).

    Google Scholar 

  25. G. Baccolini, G. Bartoli, E. Marrota, and P. K. Todesco, J. Chem. Soc. Perkin Trans. 1, 2695 (1983).

    Google Scholar 

  26. É. D. German and R. R. Dogonadze, The Proton in Chemistry [in Russian], Mir, Moscow (1977), p. 362.

    Google Scholar 

  27. Dzh. A. Kereselidze, R. G. Gasanov, M. A. Tsikoliya, and Sh. A. Samsoniya, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2893 (1991).

  28. F. Sparatore, V. Boido, and G. Parisin, Tetrahedron Lett., No. 27, 2371 (1974).

  29. V. Kvasnicka and J. Pospichal, J. Math. Chem.,5, No. 4, 309 (1990).

    Google Scholar 

Download references

Authors
  1. Dzh A. Kereselidze
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sh A. Samsoniya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Tsikoliya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

I. Dzhavakhishvili Tbilisi State University, Tbilisi 380028. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1092–1103, August, 1995. Original article submitted August 26, 1995.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kereselidze, D.A., Samsoniya, S.A. & Tsikoliya, M.A. New scheme of the mechanism of Fischer indolization. Chem Heterocycl Compd 31, 950–961 (1995). https://doi.org/10.1007/BF01170322

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01170322

Keywords

Search

Navigation