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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, 344006, Rostov-on-Don

    T. A. Kuz'menko, V. V. Kuz'menko, A. M. Simonov & B. Ya. Simkin

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  1. T. A. Kuz'menko
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  2. V. V. Kuz'menko
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  3. A. M. Simonov
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  4. B. Ya. Simkin
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Additional information

See [1] for communication 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1656–1661, December, 1980.

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Kuz'menko, T.A., Kuz'menko, V.V., Simonov, A.M. et al. Research on imidazo[2,1-α]isoquinoline derivatives. 2. Synthesis and transformations of esters of the imidazo[2,1-α]isoquinoline series. Chem Heterocycl Compd 16, 1255–1260 (1980). https://doi.org/10.1007/BF00501830

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  • DOI: https://doi.org/10.1007/BF00501830

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