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A facile approach for synthesis of thiazines-, thiazoles- and triazoles-annulated 6-styryl-2-thiouracil derivative

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Abstract

Utility of 4-oxo-6-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 1 in synthesis of a new series of fused pyrimidines was described. Pyrimido[2,1-b][1,3]thiazines 6–9 were obtained via Michael addition of compound 1 to the polarized systems 2–5 in the presence of nanosized ZnO. S-alkylation of pyrimidine 1 followed by cyclization with phenacyl bromide, monochloroacetic acid, chloroacetonitrile and oxalyl chloride afforded the desired thiazolo[3,2-a]pyrimidines 10–13. Hydrazinolysis of compound 1 followed by addition cyclization with acetic anhydride, formic acid, carbon disulfide and benzoyl chloride afforded triazolo[4,3-a]pyrimidines 15–18. The antimicrobial screening showed high activity for thiazolo[3,2-a]pyrimidines 11 and 12 against both Gram (+ ve) and Gram (− ve) bacteria.

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Authors and Affiliations

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

    H. A. Morsy

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

    H. A. Morsy

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

    A. H. Moustafa

Authors
  1. H. A. Morsy
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  2. A. H. Moustafa
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Correspondence to H. A. Morsy.

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Morsy, H.A., Moustafa, A.H. A facile approach for synthesis of thiazines-, thiazoles- and triazoles-annulated 6-styryl-2-thiouracil derivative. J IRAN CHEM SOC 17, 119–125 (2020). https://doi.org/10.1007/s13738-019-01760-w

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  • DOI: https://doi.org/10.1007/s13738-019-01760-w

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