CONDENSED ISOQUINOLINES. 31. REACTION OF 5-ARYL-3-HALO-12H-ISOQUINO[2,3-<i>a</i>]QUINAZOLINES WITH ELECTROPHILIC REAGENTS

Authors

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

DOI:

https://doi.org/10.1007/7120

Keywords:

5-aryl-12H-isoquino[2, 3-a]quinazoline, 5-arylisoquino[2, 3-a]quinazolin-13-ium bromides, acylation borohydride reduction, oxidation

Abstract

Treatment of 5-aryl-3-halo-12H-isoquino[2,3-a]quinazolines with electrophilic reagents readily forms their oxidation products. Acylation of the 3-chloro-5-phenyl-7,12-dihydroisoquino[2,3-a]quinazolinium perchlorate with Ac2O in the presence of pyridine gave the product of electrophilic substitution at the C-7 atom 1-(3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazolin-7-yl)-1-ethanone. By the same route phenacyl bromides react with the anhydro base  1 to give 5-aryl-7-(2-aryl-2-oxoethyl)-3-halo-isoquino[2,3-a]quinazolin-13-ium bromides. These salts readily react with nucleophilic reagents to form the products of addition at the C-12 atom.

How to Cite
Potikha, L. M.; Kisil, V. M.; Turov, A. V.; Kovtunenko, V. A.  Chem. Heterocycl. Compd. 2008, 44, 838. [Khim. Geterotsikl. Soedin. 2008, 1044.]

For this article in the English edition see DOI 10.1007/s10593-008-0117-2


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Published

2022-10-07

Issue

No. 7 (2008)

Section

Original Papers