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Chemistry of Heterocyclic Compounds

, Volume 16, Issue 12, pp 1255–1260 | Cite as

Research on imidazo[2,1-α]isoquinoline derivatives. 2. Synthesis and transformations of esters of the imidazo[2,1-α]isoquinoline series

  • T. A. Kuz'menko
  • V. V. Kuz'menko
  • A. M. Simonov
  • B. Ya. Simkin
Article
  • 48 Downloads

Abstract

The action of α-halo keto acid esters on 1-aminoisoquinoline was used to synthesize 2- and 3-alkoxycarbonylimidazo[2,1-α]isoquinolines. The 2-ethoxycarbonyl and 2-ethoxycarbonylmethyl derivatives display the typical properties of esters and readily undergo electrophilic substitution (chlorination and bromination) in the 3 position of the system. 3-Alkoxycarbonyl-substituted compounds in which the ester group is attached to the carbon atom with increased electron density do not react with amines; the acid hydrolysis of these compounds is accompanied by elimination of carbon dioxide. Under radical bromination conditions the 3-ethoxycarbonyl-2-methyl derivative is brominated in the methyl group to give monobromoand dibromo-substituted compounds.

Keywords

Methyl Ester Hydrolysis Dioxide Carbon Dioxide 
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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Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • T. A. Kuz'menko
    • 1
  • V. V. Kuz'menko
    • 1
  • A. M. Simonov
    • 1
  • B. Ya. Simkin
    • 1
  1. 1.Scientific-Research Institute of Physical and Organic ChemistryRostov State UniversityRostov-on-Don

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