Utility of 3-chloro-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal for construction of novel heterocyclic systems: aynthesis, characterization, antimicrobial and anticancer evaluation

Abstract

3-Chloro-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal (2) was utilized as a synthetic intermediate for construction of a variety of heterocyclic system linked furo[3,2-g]chromene (khellin) moiety. Reaction of compound 2 with some heterocyclic amines produced the Schiff bases 5 and 6. Treatment of compound 2 with a diversity of 1,2-, 1,3- and 1,4-binucleophilic reagents afforded a diversity of furo[3,2-g]chromenes bearing pyrazoles, pyridines, pyrimidine, pyrazolopyridine, triazolo[4,3-a]pyrimidine, pyrimido[1,2-a]benzimidazole, pyrido[1,2-a] benzimidazole, pyrido[2,3-d]pyrimidine, pyrazolo[3,4-b]pyridine, benzodiazepine, benzoxazepine and benzothiazepine. The prepared compounds were screened for their antimicrobial and anticancer activities demonstrating variable inhibitory effect. Analytical and spectral data were used to verify the structures of the newly prepared compounds.

Graphical Abstract

Keywords:

• Furo[3,2-g]chromene
• β-chloroenaldehyde
• pyrimidine
• nucleophilic reactions
• nitrogen heterocycles