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

Authors

  • Александр В. Комков N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Михаил А. Козлов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Юрий А. Линицкий N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991 D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047
  • Леонид С. Васильев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Андрей С. Дмитренок N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Игорь В. Заварзин N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/6248

Keywords:

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

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

Author Biography

Юрий А. Линицкий, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991 D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047

Российский химико-технологический университет им. Д. И. Менделеева,
Миусская пл., 9, Москва 125047

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Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers