Synthesis and antitubercular activity evaluation of 4-furano-coumarins and 3-furano-chromones

Abstract

The synthesis of novel 4-furano-coumarins and 3-furano-chromones has been achieved using silver-mediated oxidative C–H/C–H functionalization of 4-ethynylcoumarin/3-ethynylchromone with ethyl acetoacetate in 80%–90% and 82%–90% yields, respectively. The structure of the synthesized compounds was established on the basis of their spectral data analysis and the structure of one of the 4-furano-coumarins has been further confirmed on the basis of its X-ray crystallographic study. All eight synthesized 4-furano-coumarins and 3-furano-chromones exhibited moderate antitubercular activity against sensitive reference strain H37Rv of Mycobacterium tuberculosis.

Graphical Abstract

Keywords:

• 3-Furano-chromone
• 4-furano-coumarin
• antitubercular activity
• C–H/C–H functionalization

Acknowledgments

We are thankful to CIF-USIC University of Delhi for providing crystallographic data and NMR spectral recording facility.

Additional information

Funding

We are grateful to the University of Delhi for providing financial support under DU-DST Purse Grant and under scheme to strengthen research and development. A.S. thanks DRDO for the Junior Research Fellowship. D.B. and R.K. thank CSIR for Senior Research Fellowship.