A series of fused nicotinonitrile derivatives was synthesized by reaction of 2,6-dioxonicotinonitrile derivative 1 with different electrophilic reagents. Reaction of pyridone 1 with benzyledine derivative 2, 3 and 7 afforded pyrano[2,3-b] pyridine 4 and 11 derivatives, respectively. Upon reaction of pyridone 1 with α,β-unsaturated carbonyl compounds and benzoyl isothiocyanate gave the corresponding pyridine derivatives 11-13 and 16, respectively, Morevere sulfurization and selenation of pyridone 1 with sulfur and selenium in the presence of triethyl amine afforded the fused pyridine 14 and 15, respectively. The structure of the new synthesized compounds was elucidated by IR, NMR and elemental analysis. Some of new synthesized pyridines were screnned for anticancer activity.