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


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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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).

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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