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Indole derivatives

CXI. Introduction of a 3-indolyl group in CH acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method for the introduction of a 3-indolyl group in compounds with an active methylene group was developed. The corresponding 3-indolyl diketones were obtained by condensation of 1-acetyl-3-indolinone with dimedone, 4-hydroxycoumarin, 1,2-diphenyl-3,5-pyrazolinedione, and barbituric and thiobarbituric acids and subsequent alkaline hydrolysis of the condensation products. The existence of cyclic six-membered 3-indolyl diketones in the enol form and of cyclic five-membered 3-indoly diketones in the keto form was shown by IR and UV spectroscopy. Depending on the conditions, (1-acetyl-3-indolyl)cyanoacetamide, 1,3-bis(1-acetyl-3-indolyl)-1,3,3-tricyano-2-amino-1-propene, and 1-acetyl-3-indolylmalononitrile are obtained in the condensation of 1-acetyl-3-indolinone with malononitrile. 1-Acetyl-3-indolylmalononitrile exists in equilibrium with the keteneimine form and in protic solvents is converted to 3-cyano-8-acetylpyrrolo[2,3-b]indole by intramolecular cyclization.

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Authors and Affiliations

  1. D. I. Mendeleev Moscow Chemical-Engineering Institute, 125047, Moscow

    V. S. Velezheva, V. P. Sevodin, Yu. V. Erofeev, N. K. Genkina, T. A. Kozik, V. V. Vampilova & N. N. Suvorov

Authors
  1. V. S. Velezheva
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  2. V. P. Sevodin
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  3. Yu. V. Erofeev
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  4. N. K. Genkina
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  5. T. A. Kozik
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  6. V. V. Vampilova
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  7. N. N. Suvorov
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Additional information

See [1] for communication CX.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 360–368, March, 1977.

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Velezheva, V.S., Sevodin, V.P., Erofeev, Y.V. et al. Indole derivatives. Chem Heterocycl Compd 13, 290–297 (1977). https://doi.org/10.1007/BF00470313

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  • DOI: https://doi.org/10.1007/BF00470313

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