Abstract
A series of substituted 4H-pyrano[2,3-d]pyrimidines were synthesized from corresponding substituted 4H-pyrans by ring-closing reaction with acetic anhydride or acetic acid in the presence of trifluoroacetic acid as catalyst. The successive alkylation reaction of lactam N–H bond on pyrimidine-4-one ring was carried out using propargylic bromide in dry acetonitrile in the presence of anhydrous potassium carbonate. Three procedures applied for this purpose, including MW-assisted heating conditions at power of 100 W, under conventional heating conditions in water bath at 50 °C, and under ultrasound-assisted heating conditions at 50 °C. Dry acetonitrile was used as reaction solvent. Excellent yields of N-propargyl-4H-pyrano[2,3-d]pyrimidine derivatives were obtained. The single-crystal X-ray structure of compound 6a has been recorded, and the study helps to confirm the structure of synthesized N-propargyl derivative of 4H-pyrano[2,3-d]pyrimidines 6a–6p.
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This research is funded by Vietnam National Foundation for Science and Technology Development (NAFOSTED) under Grant Number 104.01-2020.01.
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Hai, D.S., Ha, N.T.T., Tung, D.T. et al. N-propargylation reaction of substituted 4H-pyrano[2,3-d]pyrimidine derivatives under conventional, ultrasound- and microwave-assisted conditions. Chem. Pap. 76, 5281–5292 (2022). https://doi.org/10.1007/s11696-022-02213-0
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DOI: https://doi.org/10.1007/s11696-022-02213-0