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Functionalization of Ethyl 6-Amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate: Facile Synthesis of a New Series of Pyrano[2,3-d]pyrimidine Derivatives

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Abstract

Herein, synthesis of a new series of pyrano[2,3-d]pyrimidine scaffolds is presented. Ethyl 6-amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate has been reacted with formamide, formic acid, urea, thiourea, semicarbazide, and thiosemicarbazide to give six new pyrano[2,3-d]pyrimidine derivatives in moderate to high yields (48–78%). Acylation and intramolecular cyclization of pyran with carbon disulfide, ethyl cyanoacetate, acetic anhydride, or chloroacetyl chloride has resulted in formation of the corresponding desired bicyclic pyrimidine derivatives. The chloromethyl derivative was subjected to nucleophilic substitution by its reaction with morpholine, piperidine or aniline resulting in the corresponding 2-substituted pyrimidine derivatives in good yields.

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Authors and Affiliations

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

    H. A. El-Sayed, S. A. Said & A. Abd El-Hamid

  2. Department of Medical Laboratories, Higher Institute of Medical Sciences and Technology-Abu Slim Tripoli, 21821, Tripoli, Libya

    A. S. A. Mohamed

  3. Pharmaceutical Chemistry Department, Drug Exploration and Development Chair, College of Pharmacy, King Saud University, 11451, Riyadh, Saudi Arabia

    A. E. Amr

  4. Applied Organic Chemistry Department, National Research Center, El-Dokki, 12622, Cairo, Egypt

    A. E. Amr

  5. Higher Institution of Engineering and Modern Technology, Elmarg, 13774, Cairo, Egypt

    H. A. Morsy

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  1. H. A. El-Sayed
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  2. S. A. Said
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  3. A. Abd El-Hamid
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  4. A. S. A. Mohamed
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  5. A. E. Amr
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Correspondence to H. A. El-Sayed.

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El-Sayed, H.A., Said, S.A., El-Hamid, A.A. et al. Functionalization of Ethyl 6-Amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate: Facile Synthesis of a New Series of Pyrano[2,3-d]pyrimidine Derivatives. Russ J Gen Chem 91, 1403–1408 (2021). https://doi.org/10.1134/S1070363221070203

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