Abstract
2-Thiouracil-5-sulphonic acidN-(4-acetylphenyl) Amide (1) was reacted with a series of aromatic aldehydes giving chalcones2 (Claisen-Schemidt reaction), some of these chalcones were reacted with urea and thiourea giving pyrimidine-2-one and pyrimidine-2 thione derivatives respectively of the type3a,b and4a,b. In addition many chalcones were reacted with hydroxylamine hydrochloride giving isoxazoline derivatives5a,b. They could also reacted with Phenylhydrazine to give pyrazoline derivatives6a,b, chalcones also were reacted withethylcyano acetate and/or malononitryl in pyridine giving pyran derivatives7a,c and8a,c In another pathway chalcones were epoxidised by H2O2 giving epoxides9a,c which in turn were reacted with Phenylhydrazine giving 4-hydroxypyrazoline derivatives10a,c. In another reaction chalcones were reacted with ethylcyanoacetate in presence of amm.acetate giving pyridone derivatives11a,d which could be prepared also in exellent yield from compound 1 by its reaction with certain aromatic aldehydes and ethylcyanoacetate in presence of ammonium acetate. Finally, compound 1 was reacted with semicarbazide giving semicarbazone intermediate12 which in turn was reacted with thionyl chloride giving thiadiazole derivative13. The biological effects of some of the new synthesized compounds were also investigated.
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Fathalla, O.A., Awad, S.M. & Mohamed, M.S. Synthesis of new 2-thiouracil-5-sulphonamide derivatives with antibacterial and antifungal activity. Arch Pharm Res 28, 1205–1212 (2005). https://doi.org/10.1007/BF02978199
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DOI: https://doi.org/10.1007/BF02978199