2-Cyano-N-(3-cyano-4,6-dimethyl-2-oxopyridin-1-yl)acetamide (3) was prepared via two routes and its reactions with various aldehydes and diazonium salts were studied. When compound 3 was treated with arylidenemalononitrile in either ethanol or dioxane using piperidine as a catalyst in a trial to prepare bispyridone derivatives 7, there was no reaction and the reason for this was investigated using molecular modeling. Furthermore, coumarin derivatives 9 and 10 were prepared by reaction of acetamide 3 with salicylaldehyde derivatives. Finally, aminopyrazole derivatives 15 were synthesized by reaction of acetamide 3 with N,N-dimethylformamide dimethyl acetal (DMFDMA) then with hydrazine derivatives and their mechanisms was discussed.