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


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.


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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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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