The essential aim of the present study is designed to utilize 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) to build some novel heterocyclic systems containing benzofurans as well as furo[3,2-g]chromenes. Ring opening ring closure reactions of compound 1 with N-phenyl-2-cyanoacetamide produced 8-amino-furochromenopyridine-7-carboxamide 2, which cyclized with some electrophilic reagents giving furochromenopyridopyrimidines (63–73% yields). The reaction of carbonitrile 1 with pyrazolone derivatives yielded furochromenopyrazolopyridines 10 and 11 in good yields. Also, benzo[h]furochromeno naphthyridine 13 was synthesized from recyclization of carbonitrile 1 with 1-ethyl-4-hydroxyquinolin-2(1H)-one (12). On a different mechanism, recyclization of carbonitrile 1 with some 1,3-binucleophiles afforded pyrido[2,3-d]pyrimidines (14 and 15), pyrimido[1,2-a]pyrimidine 17 and pyrimido[2,1-c][1,2,4]triazine 19 in suitable yields (62–71%). Finally, the reaction of carbonitrile 1 with 1,3-cyclohexanedione and 1,4-cyclohexanedione in 2:1 molar ratio yielded polyfused systems 20 and 21, respectively. Based on spectral and analytical results, the structures of the all products were inferred.