Skip to main content
SpringerLink
Log in

Stereodirected Catalytic Synthesis of Perhydroacridines and Their Isologs from Decahydroacridine-1,8-diones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The catalytic reduction of decahydroacridine-1,8-diones has been studied under hydrogen pressure in the presence of Raney nickel and with nascent hydrogen from alkaline treatment of nickel–aluminum alloy. Conditions have been developed for the stereodirected synthesis of 8-hydroxy-cis-dodecahydroacridin-1-ones and perhydroacridines of the cis-syn-cis and cis-anti-cis configurations. The structure of the hydroacridines was established by 1H NMR spectroscopy, 13C, and IR spectra, and chromato-mass spectrometry.

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. T. G. Nikolaeva, Yu. M. Shchekotikhin, A. S. Ponomarev, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 475 (2000).

  2. Yu. M. Shchekotikhin, Yu. A. Getmanenko, T. G. Nikolaeva, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 1344 (2001).

  3. E. I. Stankevich and G. Ya. Vanag, Izv. Akad. Nauk LatvSSR, Ser. Khim., 223 (1961).

  4. H. Antaki, J. Chem. Soc., 2263 (1965).

  5. I. N. Gracheva and A. I. Tochilkin, Khim. Geterotsikl. Soedin., 77 (1988).

  6. L. K. Keefer and G. Lunn, Chem. Rev., 89, 459 (1989).

    Google Scholar 

  7. J. Baldas and Q. N. Porter, Tetrahedron Lett., 1351 (1968).

  8. C. Dagher, R. Hanna, P. B. Terentiev, Y. G. Boundel, N. Kost, and B. I. Maksimov, J. Heterocycl. Chem., 19, 645 (1982).

    Google Scholar 

  9. P. Cupka, J. Bella, and A. Martvon, Coll. Czech. Chem. Commun., 52, 742 (1987).

    Google Scholar 

  10. C. A. Grob and H. R. Kiefer, Helv. Chim. Acta, 48, 799 (1965).

    Google Scholar 

  11. V. I. Alekseev, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 235 (1975).

  12. A. P. Kriven'ko, T. G. Nikolaeva, L. M. Yudovich, N. T. Komyagin, A. I. Yanovskii, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., 1645 (1987).

  13. T. G. Nikolaeva, L. M. Yudovich, A. A. Pastukhova, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 200 (1992).

  14. T. G. Nikolaeva, P. V. Reshetov, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 867 (1997).

  15. V. G. Kharchenko, L. M. Yudovich, N. S. Smirnova, G. I. Rybina, and L. I. Markova, Zh. Org. Khim., 23, 576 (1987).

    Google Scholar 

  16. G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York (1972), 240 pp.

    Google Scholar 

  17. D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 94, 5318 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Saratov N. G. Chernyshevskii State University, Saratov, 410026, Russia

    T. G Nikolaeva

  2. Nita-Farm ZAO, Saratov, 410005, Russia

    Yu. M. Shchekotikhin

Authors
  1. T. G Nikolaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. M. Shchekotikhin
    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

Nikolaeva, T.G., Shchekotikhin, Y.M. Stereodirected Catalytic Synthesis of Perhydroacridines and Their Isologs from Decahydroacridine-1,8-diones. Chemistry of Heterocyclic Compounds 40, 582–593 (2004). https://doi.org/10.1023/B:COHC.0000037313.98113.1e

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:COHC.0000037313.98113.1e

Search

Navigation