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Abstract The addition of cyanomethylene derivative 2 to aroyl isothiocyanate 1 afforded mercaptopyrimidine derivative 5. Mercaptopyrimidine 11 was prepared and transformed upon alkylation with chloroacetamide to thienopyrimidine 13. Oxidation of 11 using I2/AcOH yielded the disulphide 14, while oxidation using H2O2/AcOH gave pyrimidine derivative 15. Reaction of aldehydes with aminothiouracil 16 yielded 5-aroyl-2,8-di-thioxo-2,3,5,8,9,10-hexahyDROPyrimido[5’,4’:5,6]pyrido[2,3-d]pyrimidine derivative 19a,b. Addition of 16 to chalcone afforded pyridopyrimidine 20. Reaction of urea, α-naphthaldehyde and aminothiouracil afforded pyrimidopyrimidine 21. Reaction of 16 with NH4SCN afforded compound 22 that oxidized to bis-isothiazolopyrimidine bisulphide 23. |