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A facile synthesis of highly fluorescent pyrido[2,3-d]pyrimidines and 1,8-naphthyridines via oxazine transformation and enaminic addition reactions

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Abstract

Abstract

The synthesis and fluorescence properties of highly substituted bicyclic pryridine derivatives are described. 2-Substituted-4-oxo-pyrido[2,3-d]pyrimidines 2–8 resulted from the acylation reaction of α-aminonicotinonitrile 1 with aroyl chlorides, diethyl malonate, morpholine-4-carboxylate, acetic anhydride or formic acid under solvent-free conditions. [4 + 2] Cyclocondensation and cycloaddition reactions of compound type 1 with formamide and ammonium thiocyanate tolerated the fused pyrimidines 9 and 11, respectively. Finally, the Friedländer-like reaction was applied for the synthesis of 1,8-naphthyridines 12–15 via reaction of compound 1 with cyclohexanone, dimedone, acetyl acetone and benzyl methyl ketone, respectively, under AlCl3 catalysis. The fluorescence spectroscopic data of compounds 1–4, 6–8, 11, 12, 14 and 15 measured and significant results were observed.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Zagazig University, 44519, Zagazig, Egypt

    Hassan A. El-Sayed

  2. Higher Institution of Engineering and Modern Technology, Elmarg, Cairo, Egypt

    Hesham A. Morsy

  3. Agriculture Research Center, Soils, Water and Environment Research Institute, 9 El-Gammah St. El, Giza, Egypt

    Hesham A. Morsy

Authors
  1. Hassan A. El-Sayed
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  2. Hesham A. Morsy
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Correspondence to Hassan A. El-Sayed.

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El-Sayed, H.A., Morsy, H.A. A facile synthesis of highly fluorescent pyrido[2,3-d]pyrimidines and 1,8-naphthyridines via oxazine transformation and enaminic addition reactions. J IRAN CHEM SOC 16, 723–732 (2019). https://doi.org/10.1007/s13738-018-1548-z

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  • DOI: https://doi.org/10.1007/s13738-018-1548-z

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