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Synthesis of substituted tryptanthrins via oxidation of isatin and its derivatives

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Abstract

Oxidation of isatin and its 5-substituted analogs with potassium permanganate in anhydrous acetonitrile gave indolo[2,1-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-dichloroindolo[2,1-b]quinazoline-6,12-dione, while 1,4-dichloroindolo[2,1-b]quinazoline-6,12-dione and 1,4-dichloro-8-methylindolo[2,1-b]quinazoline-6,12-dione were obtained by oxidative coupling of 4,7-dichloroisatin with isatin and 5-methylisatin, respectively.

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Authors and Affiliations

  1. Far East Federal University, ul. Oktyabr’skaya 27, Vladivostok, 690000, Russia

    T. V. Moskovkina

  2. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok, Russia

    M. V. Denisenko, A. I. Kalinovskii & V. A. Stonik

Authors
  1. T. V. Moskovkina
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  2. M. V. Denisenko
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  3. A. I. Kalinovskii
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  4. V. A. Stonik
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Correspondence to T. V. Moskovkina.

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Original Russian Text © T.V. Moskovkina, M.V. Denisenko, A.I. Kalinovskii, V.A. Stonik, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 12, pp. 1760–1763.

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Moskovkina, T.V., Denisenko, M.V., Kalinovskii, A.I. et al. Synthesis of substituted tryptanthrins via oxidation of isatin and its derivatives. Russ J Org Chem 49, 1740–1743 (2013). https://doi.org/10.1134/S1070428013120051

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  • DOI: https://doi.org/10.1134/S1070428013120051

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