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Chemistry of indole

XXXIX. Orientation during the nitration of 5-hydroxyindole derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

5-Methoxy-3-carbethoxyindoles are nitrated primarily in the 4 position. Replacement of the methoxy group by an acetoxy group leads to a change in orientation — only the 6 isomer is obtained. In the case of the similarly constructed 5-hydroxyindoles, monosubstitution cannot be accomplished under various conditions, and only the 4,6-dinitro derivative is formed. The synthesis of the corresponding amines by reduction of the nitro compounds is described.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, USSR

    E. Ya. Zinchenko, L. G. Yudin & A. N. Kost

Authors
  1. E. Ya. Zinchenko
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  2. L. G. Yudin
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  3. A. N. Kost
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Additional information

See [1] for communication XXXVIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1646–1653, December, 1973.

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Zinchenko, E.Y., Yudin, L.G. & Kost, A.N. Chemistry of indole. Chem Heterocycl Compd 9, 1490–1496 (1973). https://doi.org/10.1007/BF00477564

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  • DOI: https://doi.org/10.1007/BF00477564

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