Skip to main content
SpringerLink
Log in

Annelation of the Pyrrole to the Steroid Skeleton Using the Trofimov Reaction

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The product of annelation of the N-vinyl pyrrole ring with steroid skeleton of 5-cholestene was obtained in a single regioselective step by the reaction of 5-cholesten-3-one oxime with acetylene in KOH-DMSO by the Trofimov reaction.

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. B. A. Trofimov, Heteroatomic Derivatives of Acetylene: New Polyfunctional Monomers, Reagents, and Intermediates [in Russian], Nauka, Moscow (1981).

    Google Scholar 

  2. B. A. Trofimov and N. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk (1984).

    Google Scholar 

  3. B. A. Trofimov, in: A. R. Katritzky (ed.), Adv. Heterocycl. Chem., Acad. Press, San Diego (1990), Vol. 51, 177.

    Google Scholar 

  4. B. A. Trofimov, in: R. A. Jones (ed.), Pyrroles. The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Intersci., Wiley, New York (1992), Pt. 2, 131.

    Google Scholar 

  5. A. F. Pozharskii, V. A. Anisimova, and E. B. Tsupak, Prakticum on the Chemistry of Heterocycles [in Russian], Rostov University Press, Rostov (1988), 9.

    Google Scholar 

  6. R. J. Tedeshci, in: Encyclopedia of Physical Science and Technology, Acad. Press, San Diego (1992), Vol. 1, 27.

    Google Scholar 

  7. G. P. Bean, in: R. A Jones (ed.), Pyrroles. The Synthesis and the Chemical and Physical Properties of the Pyrrole Ring, Intersci. Wiley, New York (1992), Pt. 1, 105.

    Google Scholar 

  8. B. A. Trofimov, A. M. Vasil′tsov, E. Yu. Shmidt, O. V. Petrova, and A. I. Mikhaleva, Zh. Org. Khim., 30, 576 (1994).

    Google Scholar 

  9. A. V. Afonin, I. A. Ushakov, O. A. Tarasova, E. Yu. Schmidt, A. I. Mikhaleva, and V. K. Voronov, Zh. Org. Khim., 36, 1831 (2000).

    Google Scholar 

  10. S. S. Korde, R. Katoch, R. A. Udasi, and G. K. Trivedi, Magn. Res. Chem., 37, 594 (1999).

    Google Scholar 

  11. B. A. Trofimov, A. M. Vasil′tsov, E. Yu. Schmidt, A. B. Zaitsev, A. I. Mikhaleva, and A. V. Afonin, Synthesis, 1521 (2000).

  12. B. M. Trost and E. Keiman, J.Org.Chem., 45, 2741 (1980).

    Google Scholar 

  13. E. J. Corey and J. W. Suggs, Tetrahedron Lett., 2647 (1975).

  14. E. J. Parish and S. Chitrokorn, Org. Prep. Proc. Int., 15, 365 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    A. M. Vasil'tsov, A. B. Zaitsev, A. I. Mikhaleva, E. Yu. Shmidt & A.V. Afonin

Authors
  1. A. M. Vasil'tsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. B. Zaitsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Mikhaleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Yu. Shmidt
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A.V. Afonin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vasil'tsov, A.M., Zaitsev, A.B., Mikhaleva, A.I. et al. Annelation of the Pyrrole to the Steroid Skeleton Using the Trofimov Reaction. Chemistry of Heterocyclic Compounds 38, 60–64 (2002). https://doi.org/10.1023/A:1014803325701

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1014803325701

Search

Navigation