Utility of 4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromene-6-Carbonitrile for Construction of some Novel Heteroannulated Furochromenopyridines

Abstract

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.

Keywords:

• Nucleophilic reactions
• cyclocondensation
• furo[32-g]chromene
• furochromenopyridopyrimidines

Acknowledgments

The authors extend their appreciation to Princess Nourah bint Abdulrahman University Researchers Supporting Project number (PNURSP2023R103), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.

Disclosure statement

No potential conflict of interest was reported by the author(s).