Abstract
As a part of ongoing studies in developing new potent antioxidant agents, 2-amino-4-(furan-2-yl)-5,6-dimethylnicotinonitrile 4 was utilized as a key intermediate for the synthesis of some new pyrimidines 5 and 11, form (acet)amide 6, 7, urea and thiourea 9, 10, 1,8-naphthyridines 12, 13, and 14. Moreover, condensation of 4 with 5,5-dimethyl-1,3-cyclohexanedione and cyclohexanone in ethanol furnished the pyridine derivatives 16 and 17, respectively. Furthermore, refluxing of 4 with ethylenediamine in carbon disulfide afforded the 4,5-dihydro-1H-imidazol-2-yl pyridine derivative 19. In addition, refluxing of 4 with carbon disulfide and concentrated sulfuric acid furnished the pyridine derivatives 20 and 21, respectively. The reaction of 4 with phenacyl chloride and ethyl chloroacetate in dimethylformamide in the presence of catalytic amount of triethylamine afforded the pyridine derivatives 22 and 23, respectively. Finally, heating of 4 with 1-phenyl-3-(piperidin-1-yl)propan-1-one hydrochloride in glacial acetic acid afforded phenylpropylamino pyridine derivative 24. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, H-1-NMR, and mass spectral data. Representative compounds of the synthesized products were evaluated as antioxidant agents. Compounds 8, 19, and 22 are promising compounds.