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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Notes

  1. Here and below in the experimental section, an asterisk (*) denotes signals common to both rotamers.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Alexander V. Komkov, Mikhail A. Kozlov, Yurii A. Linitskii, Leonid S. Vasil’ev, Andrey S. Dmitrenok & Igor V. Zavarzin

  2. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq, Moscow, 125047, Russia

    Yurii A. Linitskii

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  1. Alexander V. Komkov
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  2. Mikhail A. Kozlov
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  3. Yurii A. Linitskii
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  4. Leonid S. Vasil’ev
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  5. Andrey S. Dmitrenok
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Correspondence to Mikhail A. Kozlov.

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Leonid S. Vasil’ev is deceased

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 772–786

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Komkov, A.V., Kozlov, M.A., Linitskii, Y.A. et al. Synthesis of new 5-hydroxyquinazoline derivatives from functionalized 5-acetyl-6-methylpyrimidines. Chem Heterocycl Comp 57, 772–786 (2021). https://doi.org/10.1007/s10593-021-02981-9

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  • DOI: https://doi.org/10.1007/s10593-021-02981-9

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