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Using of 4-amino-2-phenylindoles in the synthesis of pyrroloquinolines by the combes reaction

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Abstract

The reaction of 4-amino-2-phenyl- and 4-amino-l-methyl-2-phenylindoles with a free β-position of the pyrrole ring with acetylacetone and dibenzoylmethane was studied. It was found that primary condensation occurs only on aminogroups and produces the corresponding enaminoketones, which under conditions of enamine acidic cyclization on the basis of dibenzoylmethane, turn into pyrrolo[2,3-h]-quinolines. The products of cyclization with participation of indole 3 atom were not detected.

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Authors and Affiliations

  1. Mordovian State Pedagogical Institute, Saransk, 43007, Russia

    E. A. Alyamkina, S. A. Yamashkin & N. N. Artayeva

  2. Division of Organic Chemistry, Moscow State University, Moscow, Russia

    M. A. Yurovskaya

Authors
  1. E. A. Alyamkina
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  2. S. A. Yamashkin
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  3. N. N. Artayeva
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  4. M. A. Yurovskaya
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Corresponding author

Correspondence to M. A. Yurovskaya.

Additional information

Original Russian Text © E.A. Alyamkina, S.A. Yamashkin, N.N. Artayeva, M.A. Yurovskaya, 2010, published in Vestnik Moskovskogo Universiteta. Khimiya, 2010, No. 5, pp. 402–408.

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Alyamkina, E.A., Yamashkin, S.A., Artayeva, N.N. et al. Using of 4-amino-2-phenylindoles in the synthesis of pyrroloquinolines by the combes reaction. Moscow Univ. Chem. Bull. 65, 335–340 (2010). https://doi.org/10.3103/S0027131410050111

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  • DOI: https://doi.org/10.3103/S0027131410050111

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