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Synthesis, properties, and mass-spectrometric fragmentation of 2-thio derivatives of 3-arylquinazolin-4-ones
Azev,Golomolzin,Dyulcks,Klyuev,Yatluk
, p. 356 - 361 (2008/09/21)
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.
