Abstract
2-Cyano-N-(antipyrin-4-yl)-3-(ethylthio)-3-(naphthalen-1-ylamino)acryl-amide 4 was achieved via a one-pot, three-component reactions of cyanoacetamide derivative 2, 2-naphthyl isothiocyanate, and diethyl-sulphate. The cyano acrylamide derivative 4 was hydrazinolysis to furnish 5-aminopyrazole 5; many pyrazolo[1,5-a]pyrimidines 10a,b, 14, 15, 16, 18, and 20 have been synthesized via treatment of 5 with some electrophilic reagents. Also, ternary condensation of cyanoacetamide derivative 2, terephthalaldehyde, and active methylene derivatives afforded bispyridone derivatives 21a,b. The structures of the new compounds were confirmed on the basis of elemental analysis and spectral data. Representative compounds of the synthesized products were tested and evaluated as antimicrobial. In general, the novel-synthesized compounds showed a good antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria, and antifungal activity against Azithromycin and Ketoconazole. The molecular modeling of the 21a and 21b as representative examples of the synthesized compounds has been drawn, and their molecular parameters were calculated.