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Chemistry of Heterocyclic Compounds

, Volume 28, Issue 1, pp 43–47 | Cite as

1-Acetyl-2-chloro-3-iminoindoline hydrochloride and its N-acetyl derivatives in nucleophilic substitution reactions

  • V. S. Velezheva
  • S. Yu. Ryabova
  • A. I. Mel'man
  • V. I. Pol'shakov
Article

Abstract

It is shown that the chlorine atom in position 2 of 1-acetyl-2-chloro-3-iminoindoline hydrochloride is readily substituted on treatment with secondary amines and thiophenol. The products of nucleophilic reaction are isolated as 2-substituted 3-aminoindoles or 3-acetylaminoindoles, and as 2-substituted 1-acetyl-3-indolinones. The latter are also formed from 1-acetyl-3-indolinone by successive bromination and treatment with secondary amines.

Keywords

Organic Chemistry Chlorine Hydrochloride Chlorine Atom Secondary Amine 
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. S. Velezheva and S. Yu. Ryabova, Khim. Geterotsikl. Soedin., No. 3, 388 (1990).Google Scholar
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    V. S. Velezheva, S. Yu. Ryabova, and L. M. Alekseeva, USSR Patent 1,490,115; Byull. Izobret., No. 24, 114 (1989).Google Scholar
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    V. S. Velezheva, V. V. Dvorkin, L. I. Dmitrievskaya, and N. N. Suvorov, Zh. Org. Khim., 16, 432 (1990).Google Scholar
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    V. S. Velezheva, A. I. Mel'man, V. I. Pol'shakov, and O. S. Anisimova, Khim. Farm. Zh. (awaiting publication).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • V. S. Velezheva
    • 1
  • S. Yu. Ryabova
    • 1
  • A. I. Mel'man
    • 1
  • V. I. Pol'shakov
    • 1
  1. 1.S. Ordzhonikidze All-Union Chemical and Pharmaceutical Research InstituteMoscow

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