Condensed isoquinolines 26. Oxidation reactions of 6,11-dihydro-13H-isoquino-[3,2-<Emphasis Type="Italic">b</Emphasis>]quinazolin-13-one derivatives |
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Authors: | L M Potikha V A Kovtunenko A V Tarasevich |
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Institution: | (1) Kiev Taras Shevchenko National University, Kiev, 01033, Ukraine |
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Abstract: | Oxidation of the hydrobromide of 6,11-dihydro-13H-isoquino3,2-b]quinazolin-13-one with dimethyl sulfoxide leads to 11-hydroxy-11H-isoquino3,2-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 isoquino3,2-b]quinazolines are readily oxidized on boiling in nitrobenzene, which leads to aromatization
of the isoquino3,2-b]quinazoline system to 5-methyl-13-oxo-5H,13H-isoquino 3,2-b]quinazolinium perchlorate and 6-benzyl-13H-isoquino3,2-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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1833–1840, December, 2007. |
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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 |
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