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Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

Methods were developed for the synthesis of new pyrido[2,3-d]pyrimidine and pyrimidino[4,5-d][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-d]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization. In the presence of an activated CH2 group (e.g., PhCH2) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-d]pyrimidin-7-one derivatives. The reaction of 5-acetyl-4-aminopyrimidines with carboxylic acid chlorides under reflux in xylene followed by addition of a base affords pyrimidino[4,5-d][1,3]oxazines.

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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, Andrey S. Dmitrenok, Nataliya G. Kolotyrkina, Mikhail E. Minyaev & Igor V. Zavarzin

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  1. Alexander V. Komkov
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  2. Mikhail A. Kozlov
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  3. Andrey S. Dmitrenok
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  5. Mikhail E. Minyaev
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Correspondence to Mikhail A. Kozlov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 787–798

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Komkov, A.V., Kozlov, M.A., Dmitrenok, A.S. et al. Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines. Chem Heterocycl Comp 57, 787–798 (2021). https://doi.org/10.1007/s10593-021-02982-8

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