SYNTHESIS, PROPERTIES, AND MASS-SPECTROMETRIC FRAGMENTATION OF 2-THIO DERIVATIVES OF 3-ARYLQUINAZOLIN-4-ONES

Authors

  • Ю. А. Азев Ural State Technical University, Ekaterinburg 620002
  • Б. В. Голомолзин Ural State Technical University, Ekaterinburg 620002
  • T. Дюлькс Bremen University
  • Н. А. Клюев Institute of Ecology and Evolution Problems, Russian Academy of Sciences, Moscow 117071
  • Ю. Г. Ятлук Ural State Technical University, Ekaterinburg 620002

DOI:

https://doi.org/10.1007/7647

Keywords:

3-aryl-2-thioxoquinazolin-4-ones, alkylation, hydrolysis, mass-spectrometric fragmentation, oxidation, skeletal rearrangements, thermolysis

Abstract

We have studied the reactions of alkylation, oxidation, and hydrolysis of 3-aryl-2-thioxoquinazolin-4-ones. Alkylation in an alkaline medium occurs exclusively at the sulfur atom. Oxidation by hydrogen peroxide leads to formation of 3-arylquinazoline-2,4-diones. The latter are also obtained in base or acid hydrolysis of the synthesized S-alkyl derivatives.  When 3-aryl-2-thioxoquinazolin-4-ones are reacted with iodine, we obtain the disulfides, while the reaction with chlorine in hydrochloric acid leads to 2-chloroquinazolin-4-ones. Studying the mass spectrometric behavior of the compounds obtained made it possible to observe in the gas phase ring–chain isomerization of the heterocyclic ring, and also S–N migration of the propargyl radical in molecular ions of the S-propargyl derivatives.

How to Cite
Azev, Yu. A.; Golomolzin, B. V.; Dyulcks, T.; Klyuev, N. A.; Yatluk, Yu. G.  Chem. Heterocycl. Compd. 2007, 43, 356. [Khim. Geterotsikl. Soedin. 2007, 440.]

For this article in the English edition see DOI 10.1007/s10593-007-0052-7

 

Published

2023-03-31

Issue

No. 3 (2007)

Section

Original Papers