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Synthesis of tryptanthrin (couroupitine) derivatives by reaction of substituted isatins with phosphoryl chloride

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Abstract

Reaction of 5-methyl-, 5-bromo-, and 5-iodoisatins with phosphoryl chloride gave the corresponding 2,8-disubstituted indolo[2,1-b]quinazoline-6,12-diones in moderate yield. 5,7-Dichloroisatin failed to react with POCl3. Treatment of an equimolar mixture of isatin and 5-bromoisatin with POCl3 afforded indolo[2,1-b]-quinazoline-6,12-dione (tryptanthrin), 2,8-dibromoindolo[2,1-b]quinazoline-6,12-dione, and two isomeric monobromo-substituted tryptanthrin derivatives, the 2-bromo isomer prevailing.

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Authors and Affiliations

  1. Far East Federal University, ul. Oktyabr’skaya 27, Vladivostok, 690600, Russia

    T. V. Moskovkina

  2. Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok, Russia

    A. I. Kalinovskii & V. V. Makhan’kov

Authors
  1. T. V. Moskovkina
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  2. A. I. Kalinovskii
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  3. V. V. Makhan’kov
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Correspondence to T. V. Moskovkina.

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Original Russian Text © T.V. Moskovkina, A.I. Kalinovskii, V.V. Makhan’kov, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 1, pp. 128–131.

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Moskovkina, T.V., Kalinovskii, A.I. & Makhan’kov, V.V. Synthesis of tryptanthrin (couroupitine) derivatives by reaction of substituted isatins with phosphoryl chloride. Russ J Org Chem 48, 123–126 (2012). https://doi.org/10.1134/S1070428012010204

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  • DOI: https://doi.org/10.1134/S1070428012010204

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