Skip to main content
SpringerLink
Log in

Synthesis of 3a,4,6,7,11b,12-hexahydro-3a-methyl-7-phenylbenzo[a]furo[2,3-g]quinolizines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By alkylation of stereoisomeric 7a-methyl-2-oxo-5-phenylfuro-[2,3-c]piperidines with phenacyl bromide and subsequent reduction of the keto group by sodium borohydride, amino alcohols were obtained; heating of these products in 70% sulfuric acid affords 3a,4,6,7,11b,12-hexahydro-3a-methyl-7-phenylbenzo[a]furo[2,3-g]quinolizines. It was found that the cis-quinolizidine, upon heating to 150°C in acetic acid, is isomerized to the trans-quinolizidine.

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. E. Maryanoff, D. F. McComsey, R. J. Taylor, and J. F. Gardocki, J. Med. Chem., 24, 79 (1981).

    Google Scholar 

  2. F. T. Bruderlein, L. G. Humber, and K. Voith, J. Med. Chem., 18, 185 (1975).

    Google Scholar 

  3. F. T. Bruderlein, L. G. Humber, and K. Pelz, Can. J. Chem., 52, 2119 (1974).

    Google Scholar 

  4. C. K. Bradsher and L. E. Beavers, J. Am. Chem. Soc., 77, 453 (1955).

    Google Scholar 

  5. B. E. Maryanoff, D. F. McComsey, and B. A. Dahl-Emswiler, J. Org. Chem., 48, 5062 (1983).

    Google Scholar 

  6. G. V. Pshenichnyi, A. I. Chakhovskii, L. A. Melentovich, A. S. Zakharevskii, V. A. Mashenkov, and L. S. Stanishevskii, Khim. Geterotsikl. Soedin., No. 9, 1269 (1989).

    Google Scholar 

  7. Din' Khoang Vu, G. V. Pshenichnyi, V. A. Mashenkov, and L. S. Stanishevskii, Vestn. Belorus. Univ., Ser. 2, No. 2, 5 (1989).

    Google Scholar 

  8. G. V. Pshenichnyi, V. A. Mashenkov, and L. S. Stanishevskii, Vestn. Belorus. Univ., Ser. 2, No. 3, 21 (1988).

    Google Scholar 

  9. R. J. Schmiesing and J. R. Matz, Heterocycles, 29, 359 (1989).

    Google Scholar 

  10. S. J. Coote, S. G. Davies, D. Middlemiss, and A. Nayloir, J. Chem. Soc., Perkin Trans, 1, No. 12, 2223 (1989).

    Google Scholar 

  11. J. Barluenga, M. Tomas, A. Suarez-Sobrino, and E. Rubio, Tetrahedron Lett., 31, 2189 (1990).

    Google Scholar 

  12. R. T. Brown and M. F. Jones, Tetrahedron Lett., 25, 3127 (1984).

    Google Scholar 

  13. E. I. Levkoeva and L. N. Yakhontov, Usp. Khim., 41, 1337 (1972).

    Google Scholar 

  14. S. Peng and E. Winterfeldt, Liebigs Ann. Chem., No. 4, 313 (1990).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Belorussian State University, 220080, Minsk

    Din' Khoang Vu, G. V. Pshenichnyi, V. A. Mashenkov & L. S. Stanishevskii

Authors
  1. Din' Khoang Vu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. V. Pshenichnyi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Mashenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. S. Stanishevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1679–1682, December, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vu, D.K., Pshenichnyi, G.V., Mashenkov, V.A. et al. Synthesis of 3a,4,6,7,11b,12-hexahydro-3a-methyl-7-phenylbenzo[a]furo[2,3-g]quinolizines. Chem Heterocycl Compd 29, 1450–1453 (1993). https://doi.org/10.1007/BF00531410

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00531410

Keywords

Search

Navigation