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Short Paper | Regular issue | Vol 100, No. 9, 2020, pp.1450-1462
Published online, 8th July, 2020
DOI: 10.3987/COM-20-14294
■ Synthetic Approach for Building Heteroannulated Furo[3,2-g]chromenes Using 4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile and Cyclic Carbon Nucleophiles

Magdy A. Ibrahim,* Sami A. Al-Harbi, and Esam S. Allehyani

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11711, Egypt

Abstract

A novel series of polyfused heterocyclic systems containing furo[3,2-g]chromenes were efficiently synthesized. The reactivity of 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) was studied towards a variety of carbon nucleophilic reagents such as heterocyclic enols, heterocyclic enamines and cyclic active methylene compounds. Treatment of carbonitrile 1 with 4-hydroxycoumarin, 4-hydroxy-1-methylquinolin-2(1H)-one (3), 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one (4) afforded furodichromenopyridine 2, furochromenonaphthyridine 5, furochromenodipyridopyrimidine 6. Reaction of carbonitrile 1 with 4(6)-aminouracil and 5-amino-3-methyl-1H-pyrazole proceed through ring opening followed by cycloaddition into the nitrile group giving pyrido[2,3-d]pyrimidine 7 and pyrazolo[3,4-b]pyridine 8. Also, reaction of carbonitrile 1 with 5-amino-2,4-dihydro-3H-pyrazol-3-one (9), 2-(phenylimino)-1,3-thiazolidin-4- one (11), thiobarbituric acid and cyclohexane-1,3-dione produced the novel annulated furo[3,2-g]chromenes 10, 12-14, respectively. Cyclohexane-1,2-dione reacted with carbonitrile 1 in 1:2 molar ratio afforded bis-(furochromeno)[1,10]phenanthroline 15. The prepared compounds were screened in vitro for their antimicrobial activity and some of them appeared notable activity against the tested microorganisms.