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SYNTHESIS OF NEW 5-HYDROXYQUINAZOLINE DERIVATIVES FROM FUNCTIONALIZED 5-ACETYL-6-METHYLPYRIMIDINES

Александр В. Комков, Михаил А. Козлов, Юрий А. Линицкий, Леонид С. Васильев, Андрей С. Дмитренок, Игорь В. Заварзин
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Abstract


A new method for the synthesis of quinazolines based on the annulation of the benzene ring to 5-acetyl-6 methylpyrimidin-2-one(thione) derivatives has been proposed. Condensation of the latter at the methyl group with dimethylformamide dimethyl acetal in boiling PhH leads to the formation of 5-acetyl-6-[2-(dimethylamino)vinyl]pyrimidin-2-ones(thiones), which, when boiled with MeONa in MeOH, cyclize to 5-hydroxyquinazolin-2-ones(thiones). Similarly, 5-acetyl-6-methyl-4-(trifluoromethyl)pyrimidine was converted to 5-hydroxy-4-(trifluoromethyl)quinazoline. Quinazolines are not formed from 5-acetyl-6-methylpyrimidines condensed with dimethylformamide dimethyl acetal at the acetyl group, but 5-acetyl-6-methylpyrimidines can be used to obtain pyrido[2,3-d] pyrimidine derivatives.

Authors: Alexander V. Komkov, Mikhail A. Kozlov*, Yurii A. Linitskii, Leonid S. Vasil'ev†, Andrey S. Dmitrenok, Igor V. Zavarzin


Keywords


5-acetyl-6-methylpyrimidin-2-ones(thiones); dimethylformamide dimethyl acetal; 5-hydroxy-4-(trifluoromethyl)quinazoline; 5-hydroxyquinazolin-2-ones(thiones); base-catalyzed cyclization

Full Text: PDF (Russian) Supplementary File(s): Supporting information (18MB)


 

 

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