CONDENSED ISOQUINOLINES. 20. CHARACTERISTIC FEATURES OF THERMAL REARRANGEMENT OF 7,12-DIHYDRO-5H-ISOQUINO[2,3-<i>a</i>]QUINAZOLIN-5-ONE TO FORM 6,11-DIHYDRO-13H-ISOQUINO[3,2-<i>b</i>]QUINAZOLIN-13-ONE

Authors

  • Л. М. Потиха Taras Shevchenko National University, Kiev 01033
  • В. А. Ковтуненко Taras Shevchenko National University, Kiev 01033
  • А. В. Тарасевич Taras Shevchenko National University, Kiev 01033
  • Ж. Ж. Вольф Paul Sabatier University, Toulouse, Cedex 9.31062, France
  • Ш. Андрэ Paul Sabatier University, Toulouse, Cedex 9.31062, France

DOI:

https://doi.org/10.1007/7646

Keywords:

6, 11-dihydro-13H-isoquino[3, 2-b]quinazolin-13-one, 11H-isoquino[3, 2-b]quinazoline-6, 13-dione, oxidation, rearrangement

Abstract

We studied the dependence of the direction of  conversions for salts of angular 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one on temperature and the nature of the anion: heating in high-boiling solvents leads either to aromatization of the heterosystem or to the rearrangement product, the linear 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one. When its hydrobromide is heated in high-boiling solvents, along with dimerization of the linear isomers, processes of oxidation at the positions 6 and 11 of the heterosystem occur. The dimer obtained in the reaction with morpholine is readily cleaved, with formation of a 6-(4-morpholyl)-substituted linear compound.

How to Cite
Potikha, L. M.; Kovtunenko, V. A.; Tarasevich, A. V.; Wolf, J. G.;  André, Ch.  Chem. Heterocycl. Compd. 2007, 43, 347. [Khim. Geterotsikl. Soedin. 2007, 430.]

For this article in the English edition see DOI 10.1007/s10593-007-0051-8


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Published

2023-03-30

Issue

No. 3 (2007)

Section

Original Papers