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Indole chemistry

XXIX. Prototropic rearrangement of 3-alkyl- and 3-arylindoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Judging from the PMR spectra, the protonation of various 3-alkyl- and 3-arylindoles in sulfuric and trifluoroacetic acids proceeds primarily at the 3 position. Prototropic shift of a radical to form 2-substituted indoles occurs on heating with these acids, and better results are obtained with polyphosphoric acid. Ideas regarding the mechanism of the process are presented.

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Authors and Affiliations

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

    V. A. Budylin, A. N. Kost & E. D. Matveeva

Authors
  1. V. A. Budylin
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  2. A. N. Kost
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  3. E. D. Matveeva
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Additional information

See [1] for communication XXVIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 55–60, January, 1972.

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Budylin, V.A., Kost, A.N. & Matveeva, E.D. Indole chemistry. Chem Heterocycl Compd 8, 52–56 (1972). https://doi.org/10.1007/BF00478491

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  • DOI: https://doi.org/10.1007/BF00478491

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