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Synthesis and properties of 2-substituted 1-aryl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

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Abstract

Cyclization of 2-(N-acetyl-N-arylamino)nicotinonitriles in the presence of dry HCl gave 1-aryl-2-methyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines. It was shown that they are acylated by acetic anhydride, aroyl chlorides, and phenyl isocyanate at the methyl group and that with benzaldehyde they give styryl derivatives. It was determined by UV, IR, and NMR spectra that 2-acetonyl, 2-phenacyl, and 2-(N-phenylcarbamoylmethyl) derivatives of 1-aryl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines exist in enaminocarbonyl and imino enol forms with strong chelate-type intramolecular hydrogen bonding.

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Literature Cited

  1. N. I. Shramm and M. I. Konshin, Khim. Geterotsikl. Soedin., No. 1, 114 (1985).

    Google Scholar 

  2. Japanese Patent Application No. 52-53895; Ref. Zh., Khim., Abstract No. 7O269P (1978).

  3. N. S. Zefirov and S. S. Trach, Zh. Org. Khim., 12, 697 (1976).

    Google Scholar 

  4. R. Woodward and R. Hoffman, Conservation of Orbital Symmetry [Russian translation], Mir, Moscow (1971), p. 207.

    Google Scholar 

  5. A. I. Kol'tsov and G. M. Kheifets, Usp. Khim., 41, 877 (1972).

    Google Scholar 

  6. V. V. Lapachev, S. A. Stekhova, I. Ya. Mainagashev, M. A. Fedotov, V. E. Khall, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 802 (1986).

    Google Scholar 

  7. N. N. Shapet'ko, S. S. Berestova, V. G. Medvedeva, A. P. Skoldinov, and Yu. S. Andreichikov, Dokl. Akad. Nauk SSSR, 234, 876 (1977).

    Google Scholar 

  8. P. B. Terent'ev and A. P. Stankyavichus, Mass-Spectrometric Analysis of Biologically Active Nitrogenous Compounds [in Russian], Mokslas, Vilnius (1987), p. 121.

    Google Scholar 

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Authors and Affiliations

  1. Perm Pharmaceutical Institute, 614600, Perm

    L. M. Demina, M. Yu. Gavrilov, M. I. Vakhrin & M. E. Konshin

Authors
  1. L. M. Demina
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  2. M. Yu. Gavrilov
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  3. M. I. Vakhrin
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  4. M. E. Konshin
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1397–1401, October, 1991.

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Demina, L.M., Gavrilov, M.Y., Vakhrin, M.I. et al. Synthesis and properties of 2-substituted 1-aryl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines. Chem Heterocycl Compd 27, 1125–1129 (1991). https://doi.org/10.1007/BF00486811

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  • DOI: https://doi.org/10.1007/BF00486811

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