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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

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

    L. M. Potikha, V. A. Kovtunenko & A. V. Turov

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  1. L. M. Potikha
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  2. V. A. Kovtunenko
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  3. A. V. Turov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1059–1067, July, 2007.

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Potikha, L.M., Kovtunenko, V.A. & Turov, A.V. 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. Chem Heterocycl Compd 43, 893–899 (2007). https://doi.org/10.1007/s10593-007-0141-7

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  • DOI: https://doi.org/10.1007/s10593-007-0141-7

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