Synthesis of substituted tryptanthrins via oxidation of isatin and its derivatives |
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| Authors: | T V Moskovkina M V Denisenko A I Kalinovskii V A Stonik |
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| Institution: | 1. Far East Federal University, ul. Oktyabr’skaya 27, Vladivostok, 690000, Russia
2. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok, Russia
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| Abstract: | Oxidation of isatin and its 5-substituted analogs with potassium permanganate in anhydrous acetonitrile gave indolo2,1-b]quinazoline-6,12-dione (tryptanthrin) and its 2,8-dimethyl-, 2,8-dibromo-, and 2,8-diiodo derivatives. Oxidative coupling of 5,7-dichloroisatin with isatin under analogous conditions afforded 2,4-dichloroindolo2,1-b]quinazoline-6,12-dione, while 1,4-dichloroindolo2,1-b]quinazoline-6,12-dione and 1,4-dichloro-8-methylindolo2,1-b]quinazoline-6,12-dione were obtained by oxidative coupling of 4,7-dichloroisatin with isatin and 5-methylisatin, respectively. |
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