Synthesis of new 5-hydroxyquinazoline derivatives from functionalized 5-acetyl-6-methylpyrimidines

Autor:	L. S. Vasil'ev, Yurii A. Linitskii, Andrey S. Dmitrenok, Mikhail A. Kozlov, Igor V. Zavarzin, Alexander V. Komkov
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Annulation Trifluoromethyl chemistry Pyrimidine Organic Chemistry Quinazoline Dimethylformamide Ring (chemistry) Benzene Medicinal chemistry Methyl group
Zdroj:	Chemistry of Heterocyclic Compounds. 57:772-786
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-021-02981-9
Popis:	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.
Databáze:	OpenAIRE
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