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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 893–899 | Cite as

Condensed isoquinolines 23. Reaction of o-bromomethylphenyl-acetonitrile with anthranilic acids: Synthesis of 6H, 12H,17H-dibenzo[3,4:6,7][1,8]-naphthyridino[1,8-ab]quinazoline-6,17-diones

  • L. M. Potikha
  • V. A. Kovtunenko
  • A. V. Turov
Article

Abstract

The direction of the reaction of anthranilic acids with o-bromomethylphenylacetonitrile upon fusion depends on the temperature and nature of the substituent in the anthranilic acid. The reaction may lead to three types of products: Derivatives of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones below 150°C and to 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one or derivatives of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones above 150°C depending on the nature of the substituent in the anthranilic acid. A study was carried out on the mechanism for the formation of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones, which permitted the preparation of 6-(4-methylphenyl)-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one.

Keywords

anthranilic acid o-bromomethylphenylacetonitrile 6H,12H,17H-dibenzo[3,4:6,7][1,8]-naphthyridino[1,8-ab]quinazoline-6,17-dione 6-(4-methylphenyl)-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one 

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References

  1. 1.
    L. M. Potikha, Khim. Geterotsikl. Soedin., 899 (2007). [Chem. Heterocycl. Comp., 43, 759 (2007)].Google Scholar
  2. 2.
    L. M. Potikha, V. A. Kovtunenko, and V. M. Kisil, Khim. Geterotsikl. Soedin., 562 (2007). [Chem. Heterocycl. Comp., 43, 460 (2007)].Google Scholar
  3. 3.
    V. M. Kisil, V. A. Kovtunenko, A. V. Turov, A. K. Tyltin, and F. S. Babichev, Dokl. Akad. Nauk, 306, 628 (1989).Google Scholar
  4. 4.
    V. M. Kisil, L. M. Potikha, R. M. Gutsul, V. A. Kovtunenko, and A. V. Turov, Khim. Geterotsikl. Soedin., 113 (2006). [Chem. Heterocycl. Comp., 42, 100 (2006)].Google Scholar
  5. 5.
    V. M. Kisil, V. A. Kovtunenko, A. K. Tyltin, and F. S. Babichev, Ukr. Khim. Zh., 56, 749 (1990).Google Scholar
  6. 6.
    F. S. Babichev, V. K. Patratii, V. A. Kovtunenko, N. G. Prodanchuk, V. G. Zinchenko, and V. M. Kisil, Khim.-farm. Zh., 24, No. 5, 32 (1990).Google Scholar
  7. 7.
    L. M. Potikha, V. A. Kovtunenko, A. V. Tarasevich, J. G. Wolf, and Ch. André, Khim. Geterotsikl. Soedin., 430 (2007). [Chem. Heterocycl. Comp., 43, 347 (2007)].Google Scholar
  8. 8.
    C. A. G. Haasnoot, F. A. A. M. de Leeuw, and C. Altona, Tetrahedron, 36, 2783 (1980).CrossRefGoogle Scholar
  9. 9.
    Kh. M. Shakhidoyatov, A. Irisbaev, L. M. Yun, E. Oripov, and Ch. Sh. Kadyrov, Khim. Geterotsikl. Soedin., 1564 (1976). [Chem. Heterocycl. Comp., 12, 1286 (1976)].Google Scholar
  10. 10.
    L. M. Potikha, N. V. Danileiko, V. M. Kisil, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 1214 (2004). [Chem. Heterocycl. Comp., 40, 1052 (2004)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • L. M. Potikha
    • 1
  • V. A. Kovtunenko
    • 1
  • A. V. Turov
    • 1
  1. 1.Taras Shevchenko National UniversityKievUkraine

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