CONDENSED ISOQUINOLINES. 36. CYCLIZATION OF <i>N</i>-ALKYL-3-(2-BENZOYLBENZYL)AZOLIUM SALTS. A NOVEL METHOD OF PREPARING AZOLO[<i>b</i>]ISOQUINOLINES

Authors

  • Л. М. Потиха Taras Shevchenko Kiev National University, Kiev 01033
  • В. В. Сыпченко Taras Shevchenko Kiev National University, Kiev 01033
  • В. А. Ковтуненко Taras Shevchenko Kiev National University, Kiev 01033

DOI:

https://doi.org/10.1007/5037

Keywords:

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

Abstract

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.

How to Cite
Potikha, L. M.; Sypchenko, V. V.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2010, 46, 1096. [Khim. Geterotsikl. Soedin. 2010, 1360.]

For this article in the English edition see DOI 10.1007/s10593-010-0632-9

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Published

2019-03-14

Issue

No. 9 (2010)

Section

Original Papers