A new, efficient method for the construction of 4H-quinolizin-4-one based core structure has been successfully developed. The synthesis made use of a two step sequence including the Stobbe condenzation followed by cyclization starting from the commercially available pyridine-2-carbaldehyde. The structure of the formed 4-oxo-4H-quinolizine-2-caboxylate was fully confirmed by MS, ¹H-NMR, ¹³C?NMR, COSY, DEPT, HMBC and HSQC spectra. The ethyl carboxylate moiety was then further functionalized via direct aminolysis, benzimidazolization and aldol condensation to afford the corresponding 4-oxo-4H-quinolizine-2-carboxamides (4a-h), 4-oxo-4H-quinolizine-2-benzimidazole (7) and 2-((E)-3-(4-aminophenyl)-3-oxoprop-1-enyl)-4H-quinolizin-4-one (8), respectively in reasonable to good yields.