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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1096–1104 | Cite as

Condensed isoquinolines. 36*. Cyclization of N-alkyl-3-(2-benzoylbenzyl)azolium salts. A novel method of preparing azolo[b]isoquinolines

  • L. M. PotikhaEmail author
  • V. V. Sypchenko
  • V. A. Kovtunenko
Article

A novel method is proposed for the preparation of azolo[b]isoquinolines based on the alkylation of N-alkyl-1,3-diazoles or 1,3-thiazole derivatives using [2-(bromomethyl)phenyl](phenyl)methanone with subsequent cyclization of the quaternary azolium salts in the presence of base. The 10(11)-hydroxy derivatives of the 5,10-dihydro-1H-imidazo[1,2-b]isoquinolinium, 6,11-dihydro-5H-benzimidazo-[1,2-b]isoquinolinium, 5,10-dihydro-1H-[1, 2, 4]triazolo[4,3-b]isoquinolinium, or 5,10-dihydro[1, 3]-thiazolo[3,2-b]isoquinolinium bromides obtained in this way readily lose a molecule of water upon heating with HBr or Ac2O to give the corresponding quasi-aromatic azolo[b]isoquinolinium salts.

Keywords

benzimidazo[1,2-b]isoquinoline benzophenone imidazo[1,2-b]isoquinoline [1, 3]thiazolo-[3,2-b]isoquinoline [1,2,4]triazolo[4,3-b]isoquinoline. 

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Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • L. M. Potikha
    • 1
    Email author
  • V. V. Sypchenko
    • 1
  • V. A. Kovtunenko
    • 1
  1. 1.Taras Shevchenko Kiev National UniversityKievUkraine

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