CONDENSED ISOQUINOLINES. 26. OXIDATION REACTIONS OF 6,11-DIHYDRO-13H-ISOQUINO[3,2-<i>b</i>]QUINAZOLIN-13-ONE DERIVATIVES

Authors

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

DOI:

https://doi.org/10.1007/7316

Keywords:

6-benzyl-13H-isoquino[3, 2-b]quinazolin-13-one, isoquino[3, 2-b]quinazoline, 2-[(4-oxo-3, 4-dihydro-2-quinazolinyl)carbonyl]benzoic acid, 6-methyl-13-oxo-5H, 13H-isoquino[3, 2-b]quinazolinium perchlorate, oxidation

Abstract

Oxidation of the hydrobromide of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with dimethyl sulfoxide leads to 11-hydroxy-11H-isoquino[3,2-b]quinazoline-6,13-dione, and with hydrogen peroxide to the hydrobromide of 2-[(4-oxo-3,4-dihydro-2-quinazolinyl)carbonyl]benzoic acid. Salts of 5- and 6-alkyl-substituted isoquino[3,2-b]quinazolines are readily oxidized on boiling in nitrobenzene, which leads to aromatization of the isoquino[3,2-b]quinazoline system to 5-methyl-13-oxo-5H,13H-isoquino[3,2-b]quinazolinium perchlorate and 6-benzyl-13H-isoquino[3,2-b]quinazolin-13-one. The structures of the dehydrogenation products were established from  1H NMR and UV spectra. The interaction of the obtained compounds with NaBH4 has been studied.

How to Cite
Potikha, L. M.; Kovtunenko, V. A.; Tarasevich, A. V.  Chem. Heterocycl. Compd. 2007, 43, 1551. [Khim. Geterotsikl. Soedin. 2007, 1833.]

For this article in the English edition see DOI 10.1007/s10593-007-0240-5


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Published

2023-01-16

Issue

No. 12 (2007)

Section

Original Papers