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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 1, pp 77–85 | Cite as

Synthesis of pyrrolo[2,3-g]-and pyrrolo[3,2-f]quinolines from 5-amino-2,3-dimethyl-and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic ester

  • S. A. Yamaskhin
  • G. A. Romanova
  • E. A. Oreshkina
  • N. V. Zhukova
Article

Abstract

It has been shown that the condensation reaction of 5-amino-2,3-dimethyl-and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic ester occurs either via the trifluoromethylcarbonyl or the ester group depending upon the conditions under which it is carried out. Under thermal conditions (refluxing in diphenyl) the enaminocrotonates formed are readily converted to pyrrolo[3,2-f]quinolines and the amides cyclize in trifluoroacetic acid at 78°C to give pyrrolo[2,3-g]quinolines.

Keywords

5-amino-2,3-dimethylindole 5-amino-1,2,3-trimethylindole pyrrolo[2,3-g]quinoline pyrrolo[3,2-f]quinoline ethyl 4,4,4-trifluoroacetoacetate 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • S. A. Yamaskhin
    • 1
  • G. A. Romanova
    • 2
  • E. A. Oreshkina
    • 2
  • N. V. Zhukova
    • 2
  1. 1.Mordovian N. P. Ogarev State University, SaranskMordoviaRussia
  2. 2.M. E. Evsev’ev State Teaching Institute, SaranskMordoviaRussia

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