Synthetic Development and Assessment of Antioxidant Activity of Imino[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile and Its Derivatives

The reaction of 2-[bis(methylsulfanyl)methylidene]malononitrile with 1H-1,2,4-triazol-3-amine in N,N-dimethylformamide in the presence of anhydrous potassium carbonate led to the formation of 7-imino-5-(methylsulfanyl)-1,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile. The latter was then reacted with some nitrogen and carbon nucleophiles such as substituted anilines and active methylene compounds to afford the corresponding 5-substituted derivatives. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectra and elemental analyses. Furthermore, their potential as antioxidant agents was evaluated using DPPH and hydroxyl radical scavenging assays.