The recently synthesized 1-chloro-11-oxo-3,4-dihydro-11Hchromeno[4,3-b]quinoline-2-carboxaldehyde (1) was efficiently utilized as a key precursor to construct a diversity of polyfused systems containing chromeno[4,3b]quinoline. Reaction of compound 1 with some substituted hydrazines afforded pyrazoles annulated chromeno[4,3-b]quinoline. Treatment of compound 1 with a diversity of 1,3-N,N-binucleophiles led to pyrimidines annulated chromeno[4,3b]quinoline. In addition, a diversity of fused pyridines annulated chromeno[4,3b]quinoline were synthesized from condensation of compound 1 with a variety of 1,3-C,N-binucleophiles. Finally, the reactivity of compound 1 was tested towards a diversity of 1,4-binucleophilic reagents. Structures of the new compounds were established using spectral and analytical data.