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Transformations of ortho-methoxyaryl(hetaryl)carboxamides into quinazolin-4-one and pyrido[2,3-d]pyrimidin-4-one derivatives

Russian Chemical Bulletin volume 54, pages 1907–1914 (2005)Cite this article

Abstract

ortho-Chloroaryl(hetaryl)carboxamides containing one or two nitro groups at positions 3 and/or 5 of the ring undergo condensation accompanied by the pyrimidine ring closure on refluxing in an excess of sodium methoxide to form bicyclic products, viz., quinazolin-4-one, pyrido[2,3-d]pyrimidin-4-one, and pyrido[4,3-d]pyrimidin-4-one derivatives. The scheme of cyclization processes was proposed. The structures of the reaction products were confirmed by a number of physicochemical data, including X-ray diffraction analysis.

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Authors and Affiliations

  1. State Research Center of Antibiotics, 3a ul. Nagatinskaya, 117105, Moscow, Russian Federation

    O. B. Ryabova, V. A. Makarov, L. M. Alekseeva & V. G. Granik

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. S. Shashkov

  3. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    V. V. Chernyshev

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  1. O. B. Ryabova
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  2. V. A. Makarov
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  3. L. M. Alekseeva
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  4. A. S. Shashkov
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  5. V. V. Chernyshev
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  6. V. G. Granik
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1851–1858, August, 2005.

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Ryabova, O.B., Makarov, V.A., Alekseeva, L.M. et al. Transformations of ortho-methoxyaryl(hetaryl)carboxamides into quinazolin-4-one and pyrido[2,3-d]pyrimidin-4-one derivatives. Russ Chem Bull 54, 1907–1914 (2005). https://doi.org/10.1007/s11172-006-0057-x

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  • DOI: https://doi.org/10.1007/s11172-006-0057-x

Key words

  • dinitrobenzamide
  • quinazolin-4-one
  • pyrido[2,3-d]pyrimidin-4-one
  • 4-chloro-5-nitronicotinamide
  • pyrido[4,3-d]pyrimidin-4-one
  • 4,6-dichloro-5-pyrimidinocarboxamide
  • X-ray diffraction analysis