Skip to main content
SpringerLink
Log in

Diastereoselective synthesis of spiro derivatives of 3-substituted 2,3,4,4a,5,6-hexahydro-1H-benzo[c]quinolizines

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The cyclization via the mechanism of “tert-amino effect” of 2-(4-R-piperidino)benzaldehydes with cyclic active methylene components (Meldrum’s acid, 1,3-cyclohexanedione, and N,N-disubstituted barbituric acids) proceeded stereoselectively giving spiro-joined 2,3,4,4a,5,6-hexahydro-1H-benzo[c]quinolizines with axially oriented hydrogen atoms in the positions 3 and 4a of the benzo[c]quinolizine ring.

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. Verboom, W. and Reinhoudt, D.N., Rec. Trav. Chim., 1990, vol. 109, no. 5, p. 311.

    CAS  Google Scholar 

  2. Meth-Cohn, O., Suschiizky, H. Adv. Heterocyclic, Chem., 1996, vol. 65, p. 1.

    Article  CAS  Google Scholar 

  3. Glukhareva, T.V., Morzherin, Yu.Yu., Dyudya, L.V., Malysheva, K.V., Tkachev, A.V., Padva, A., and Bakuleva, V.A., Izv. Akad. Nauk, Ser. Khim., 2004, p. 1258.

  4. Reinhoudt, D.N., Visser, G.W., Verboom, W., Benders, P.H., and Pennings, M.L.M., J. Am. Chem. Soc., 1983, vol. 105, p. 4775.

    Article  CAS  Google Scholar 

  5. Nijhuis, W.H.N., Verboom, W., Reinhoudt, D.N., and Harkema, S., J. Am. Chem. Soc., 1987, vol. 109, p. 3136.

    Article  CAS  Google Scholar 

  6. Nijhuis, W.H.N., Verboom, W., Abu, El-Fadl, A., van Hummel, G.J., and Reinhoudt, D.N., J. Org. Chem., 1989, vol. 54, p. 209.

    Article  CAS  Google Scholar 

  7. Kelderman, E., Verboom, W., Engbersen, J.F.J., Harkema, S., Heesink, G.J.T., Lehmusvaara, E., van Hulst, N.F., Reinhoudt, D.N., Derhaeg, L., and Persoons, A., Chem. Mat., 1992, vol. 4, p. 626.

    Article  CAS  Google Scholar 

  8. Deeva, E.V., Glukhareva, T.V., Zybina, N.A., and Morzherin, Yu.Yu., Izv. Akad. Nauk, Ser. Khim., 2005, p. 1492.

  9. Deeva, E.V., Glukhareva, T.V., Tkachev, A.V., and Morzherin, Yu.Yu., Mendeleev Commun., 2006, vol. 16, no. 2, p. 82.

    Article  Google Scholar 

  10. Beke, G., Gergely, A., Szбsz, G., Szentesi, A., Nyitray, J., Barabбs, O., Harmath, V., and Matyus, P., Chirality, 2002, vol. 14, 365.

    Article  CAS  Google Scholar 

  11. D’yachenko, E.V., Glukhareva, T.V., Dyudya, L.V., Eltsov, O.V., and Morzherin, Yu.Yu., Molecules, 2005, vol. 10, p. 1101.

    Article  Google Scholar 

  12. Kaval, N., Halasz-Dajka, B., Vo-Thanh, G., Dehaen, W., van der, Eycken, J., Mбtyus, P., Loupyc, A., van der Eycken, E., Tetrahedron, 2005, vol. 61, p. 9052.

    Article  CAS  Google Scholar 

  13. Krasnov, K.A. and Kartsev, V.G., Heterocycles, 2007, vol. 71, p. 19.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ural State Technical University, Yekaterinburg, 620002, Russia

    T. V. Glukhareva, E. V. Deeva, A. Yu. Platonova, I. V. Geide & Yu. Yu. Morzherin

  2. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia

    M. I. Kodess

Authors
  1. T. V. Glukhareva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Deeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Yu. Platonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. V. Geide
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. I. Kodess
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu. Yu. Morzherin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. Yu. Morzherin.

Additional information

Original Russian Text © T.V. Glukhareva, E.V. Deeva, A.Yu. Platonova, I.V. Geide, M.I. Kodess, Yu.Yu. Morzherin, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5, pp. 757–767.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Glukhareva, T.V., Deeva, E.V., Platonova, A.Y. et al. Diastereoselective synthesis of spiro derivatives of 3-substituted 2,3,4,4a,5,6-hexahydro-1H-benzo[c]quinolizines. Russ J Org Chem 45, 743–754 (2009). https://doi.org/10.1134/S1070428009050170

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009050170

Keywords

Search

Navigation