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


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.


Methyl Ester Hydrolysis Dioxide Carbon Dioxide 
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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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