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Synthesis of 4-Hydroxy- and 4-Amino-2-Methyl-3-(2-Methylindol-3-Yl)methylquinolines and Their 6- and 8-Substituted Derivatives

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Abstract

A method has been developed for the synthesis of substituted 4-hydroxy- and 4-amino-2-methyl-3-(2-methylindol-3-yl)methylquinolines by treating the corresponding 4-hydroxy(chloro)-2-methyl-3-(3-oxobutyl)quinolines with phenylhydrazine hydrochloride. It was found that nucleophilic substitution occurred in the case of the 4-chloroquinolines together with subsequent rearrangement to give the 4-amino derivatives. The thiosemicarbazones of the corresponding 4-hydroxy-2-methyl-3-(3-oxobutyl)quinolines were also obtained.

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Authors and Affiliations

  1. Yerevan State University, Yerevan, 375025, Armenian Republic

    A. A. Avetisyan, I. L. Aleksanyan & A. A. Pivazyan

Authors
  1. A. A. Avetisyan
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  2. I. L. Aleksanyan
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  3. A. A. Pivazyan
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 554–557, April, 2005.

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Avetisyan, A.A., Aleksanyan, I.L. & Pivazyan, A.A. Synthesis of 4-Hydroxy- and 4-Amino-2-Methyl-3-(2-Methylindol-3-Yl)methylquinolines and Their 6- and 8-Substituted Derivatives. Chem Heterocycl Compd 41, 471–474 (2005). https://doi.org/10.1007/s10593-005-0173-9

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  • DOI: https://doi.org/10.1007/s10593-005-0173-9

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