Skip to main content
SpringerLink
Log in

Condensed isoquinolines. 19. Synthesis of 1′-R-spiro[6a,11b-diazabenz[e]aceanthrylene-6(7H),4′ (1′H)-pyridine]-5,7(12H)-diones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

During acylation of 7-isonicotinoyl-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one or its alkylation followed by treatment with organic bases, spirocyclization occurs with formation of derivatives of a novel heterocyclic system: 1′-acyl-and 1′-alkylspiro[7H,12H-6a,11b-diazabenz[e]aceanthrylene-6(5H),4′(1′ H)-pyridine]-5,7-diones. We have studied the spectral properties of the synthesized spirans. We have shown that 7-nicotinoyl-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one does not undergo an analogous reaction of repeated acylation, while treatment of its quaternary salt with bases leads to a complex mixture of unidentified products.

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. L. M. Potikha, N. V. Shkilna, V. M. Kisil, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 1362 (2004).

  2. V. M. Kisel, V. A. Kovtunenko, L. M. Potikha, A. K. Tyltin, V. S. Nikitchenko, and F. S. Babichev, Ukr. Khim. Zh., 58, 790 (1992).

    CAS  Google Scholar 

  3. V. A. Kovtunenko, V. M. Kisil, L. M. Potikha, A. V. Turov, F. S. Babichev, Ukr. Khim. Zh., 59, 1070 (1993).

    Google Scholar 

  4. M. Sainsbury and N. L. Uttely, J. Chem. Soc., Perkin Trans., 2109 (1977).

  5. T. Naito, O. Miyata, and I. Ninomiya, J. Chem. Soc., Chem. Commun., 11, 517 (1979).

    Google Scholar 

  6. T. Naito and I. Ninomiya, Heterocycles, 15, 735 (1981).

    CAS  Google Scholar 

  7. J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High Resolution Nuclear Magnetic Resonance Spectroscopy [Russian translation], Mir, Moscow (1968).

    Google Scholar 

  8. P. B. Terentiev and A. P. Stankevicius, Mass Spectroscopic Analysis of Biologically Active Nitrogen Bases [in Russian], Mokslas, Vilnius (1987), p. 86.

    Google Scholar 

  9. D. D. Weller and G. R. Luellen, Tetrahedron Lett., 22, 4381 (1981).

    Article  CAS  Google Scholar 

  10. V. M. Kisel, V. A. Kovtunenko, A. V. Turov, A. K. Tyltin, and F. S. Babichev, Dokl. Akad. Nauk, 306, 628 (1989).

    CAS  Google Scholar 

  11. V. M. Kisel, L. M. Potikha, A. V. Turov, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 1258 (2001).

Download references

Author information

Authors and Affiliations

  1. Taras Shevchenko Kiev National University, Kiev, 01033, Ukraine

    V. M. Kysil, L. M. Potikha, R. M. Gutsul, V. A. Kovtunenko & A. V. Turov

Authors
  1. V. M. Kysil
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. M. Potikha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. M. Gutsul
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Kovtunenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Turov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 18, see [1].

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 113–122, January, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kysil, V.M., Potikha, L.M., Gutsul, R.M. et al. Condensed isoquinolines. 19. Synthesis of 1′-R-spiro[6a,11b-diazabenz[e]aceanthrylene-6(7H),4′ (1′H)-pyridine]-5,7(12H)-diones. Chem Heterocycl Compd 42, 100–108 (2006). https://doi.org/10.1007/s10593-006-0053-y

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0053-y

Keywords

Search

Navigation