Skip to main content
Log in

Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one. Its oxidation in nitrobenzene led to the formation of 5,13,5′,13′-hexahydro[6,6′]bi[isoquino[3,2-b]quinazoline]-11,11′-dione, but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. L. M. Potikha, V. A. Kovtunenko, and A. V. Tarasevich, Khim. Geterotsikl. Soed., 1833 (2007). [Chem. Heterocycl. Comp., 43, 1550 (2007)].

    Google Scholar 

  2. S. Goya, A. Takadate, T. Tanaka, Y. Tsuruda, and H. Ogata, Yakugaku Zasshi, 100, 826 (1980); Chem. Abstr., 94, 65446 (1981).

    CAS  Google Scholar 

  3. S. Goya, A. Takadate, T. Tanaka, H. Nagayama, and O. Teisuke, Yakugaku Zasshi, 95, 333 (1975); Chem. Abstr., 83, 43153 (1975).

    CAS  Google Scholar 

  4. T. T. Kucherenko, R. Gutsul, V. M. Kisel, and V. A. Kovtunenko, Tetrahedron. 60, 211 (2004).

    Article  CAS  Google Scholar 

  5. V. A. Kovtunenko, T. T. Kucherenko, O. V. Shishkin, and V. M. Kisel, Khim. Geterotsikl. Soed., 1408 (2002). [Chem. Heterocycl. Comp., 38, 1242 (2002)].

    Google Scholar 

  6. E. Schefczik, Ger. Pat., 1951516; Chem. Abstr., 75, 37920 (1971).

    Google Scholar 

  7. E. Schefczik, Liebigs Ann Chem., 729, 83 (1969).

    Article  CAS  Google Scholar 

  8. L. M. Potikha, V. M. Kisel, N. V. Danileiko, and V. A. Kovtunenko, Khim. Geterotsikl. Soed., 715 (2004). [Chem. Heterocycl. Comp., 40, 603 (2004)].

    Google Scholar 

  9. H. Bekker, W. Berger, G. Domschke, E. Fanghänel, J. Faust, M. Fischer, F. Gentz, K. Gewald, R. Gluch, R. Mayer, K. Müller, D. Pavel, G. Schmidt, K. Schollberg, E. Seiler, and G. Zeppenfeld, Organikum [in Russian], Mir, Moscow, 1992, vol. 1, 245.

    Google Scholar 

  10. W. Borsche, M. Wagner-Roemmich, and J. Barthenheier, Liebigs Ann. Chem., 550, 160 (1942).

    Article  CAS  Google Scholar 

  11. M. A. Meyer, Bull. Soc. Chim. Fr., 51, 953 (1932).

    CAS  Google Scholar 

  12. R. D. Haworth and G. Sh. Pink, J. Chem. Soc., 2348 (1927).

  13. L. Johnson, J. Org. Chem., 41, 836 (1976).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. M. Potikha.

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.2, 273–279, February, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Potikha, L.M., Gutsul, R.M., Turov, A.V. et al. Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. Chem Heterocycl Comp 44, 208–213 (2008). https://doi.org/10.1007/s10593-008-0024-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-008-0024-6

Keywords

Navigation