CONDENSED ISOQUINOLINES. 23. REACTION OF <i>o</i>-BROMOMETHYLPHENYLACETONITRILE WITH ANTHRANILIC ACIDS: SYNTHESIS OF 6H,12H,17H-DIBENZO[3,4:6,7][1,8]NAPHTHYRIDINO[1,8-<i>ab</i>]QUINAZOLINE-6,17-DIONES

Authors

  • Л. М. Потиха Taras Shevchenko National University, Kiev 01033
  • В. А. Ковтуненко Taras Shevchenko National University, Kiev 01033
  • А. В. Туров Taras Shevchenko National University, Kiev 01033

DOI:

https://doi.org/10.1007/7452

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

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. 

How to Cite
Potikha, L. M.; Kovtunenko, V. A.; Turov, A. V.  Chem. Heterocycl. Compd. 2007, 43, 893. [Khim. Geterotsikl. Soedin. 2007, 1059.]

For this article in the English edition see DOI 10.1007/s10593-007-0141-7


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Published

2023-02-13

Issue

No. 7 (2007)

Section

Original Papers