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Chemistry of Heterocyclic Compounds

, Volume 13, Issue 10, pp 1079–1082 | Cite as

Acetals of lactams and acid amides

XX. Synthesis of hydrogenated derivatives of indole, quinoline, and 1H,1-benzazepine
  • V. G. Granik
  • A. M. Zhidkova
  • R. G. Glushkov
  • A. B. Grigor'ev
  • M. K. Polievktov
  • T. F. Vlasova
  • O. S. Anisimova
Article
  • 26 Downloads

Abstract

Hydrogenated derivatives of indole, quinoline, and 1H,1-benzazepine were synthesized by reaction of 1-methyl-2-benzoylmethylenepyrrolidine, -piperidine, and -hexahydroazepine with acryloyl chloride. Alkylation of 1-methyl-5-oxo-8-benzoyl-1,2,3,4,5,6,7,8-octahydroquinoline with triethyloxonium tetrafluoroborate and subsequent treatment with sodium ethoxide gave the corresponding acetal, the reaction of which with substituted anilines gave 1-methyl-5-arylimino-8-benzoyl-1,2,3,4,5,6,7,8-octahydroquinolines. The IR and PMR spectra of the compounds are presented.

Keywords

Amide Aniline Indole Alkylation Quinoline 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    V. G. Granik, O. Ya. Belyaeva, R. G. Glushkov, and T. F. Vlasova, Khim. Geterotsikl. Soedin., No. 8, 1106 (1977).Google Scholar
  2. 2.
    V. G. Granik, I. V. Persianova, A. M. Zhidkova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 8, 1084 (1975).Google Scholar
  3. 3.
    P. W. Hickmott and G. Scheppard, J. Chem. Soc., C, No. 8, 1038 (1972).Google Scholar
  4. 4.
    P. W. Hickmott and G. Scheppard, J. Chem. Soc., C, No. 11, 2112 (1971).Google Scholar
  5. 5.
    R. E. Ireland, Chem. Ind., No. 31, 979 (1958).Google Scholar
  6. 6.
    M. Meerwein, W. Florian, N. Schon, and G. Stopp, Ann., 641, 1 (1961).Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • V. G. Granik
    • 1
  • A. M. Zhidkova
    • 1
  • R. G. Glushkov
    • 1
  • A. B. Grigor'ev
    • 1
  • M. K. Polievktov
    • 1
  • T. F. Vlasova
    • 1
  • O. S. Anisimova
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry InstituteMoscow

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