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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 3, pp 351–356 | Cite as

The investigations in 2,3′-biquinoline series. 25*. Synthesis of 4-(2-quinolinyl)-pyrrolo[1,2-a]quinolines and 4-(2-quinolyl)-imidazo[1,2-a]quinolines

  • T. P. Glushchenko
  • A. V AksenovEmail author
  • V. I. Goncharov
Article

A method has been developed for the synthesis of 4-(2-quinolinyl)-1,2,3,3a-tetrahydropyrrolo-[1,2-a]quinolines based on the 1,3-dipolar cycloaddition reaction of α,β-unsaturated carbonyl compounds to 2,3′-biquinolinium salts. Oxidation in benzene using MnO2 gave 4-(2-quinolinyl)-pyrrolo[1,2-a]quinolines. It was found that a side product of the 1,3-dipolar cycloaddition is 7,14-di-benzoyl-6,13-di(2-quinolyl)-6a,7,13a,14-tetrahydro-7a,14a-diazadibenzo[a,h]anthracene. Reaction of 1′-phenacyl-2,3′-biquinolinium salts with hydroxylamine in acetic acid gave 4-(2-quinolyl)imidazo-[1,2-a]quinolines.

Keywords

2,3′-biquinoline 1′-R-3-(2-quinolyl)quinolinium bromides 7,14-dibenzoyl-6,13-di(2-quinolyl)-6a,7,13a,14-tetrahydro-7a,14a-diazadibenzo[a,h]anthracene α,β-unsaturated carbonyl compounds 4-(2-quinolyl)imidazo[1,2-a]quinolines 4-(2-quinolinyl)pyrrolo[1,2-a]quinolines 4-(2-quinolinyl)-1,2,3,3a-tetrahydropyrrolo[1,2-a]quinolines cyclization 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • T. P. Glushchenko
    • 1
  • A. V Aksenov
    • 1
    Email author
  • V. I. Goncharov
    • 2
  1. 1.Stavropol State UniversityStavropolRussia
  2. 2.Stavropol State Medical AcademyStavropolRussia

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