An Efficient Synthesis of Naphtho[2,3-<i>b</i>]furan-4,9-diones via Visible-Light-Mediated [3+2] Cycloaddition Reaction

Abstract

Naphtho[2,3-b]furan-4,9-dione is an important privileged structural motif which is present in natural products, drugs, and drug candidates. Herein, visible-light-mediated [3+2] cycloaddition reaction for the synthesis of naphtho[2,3-b]furan-4,9-diones and dihydronaphtho[2,3-b]furan-4,9-diones has been developed. Under environmentally friendly conditions, a variety of title compounds were delivered in good yields. This new protocol shows excellent regioselectivity and remarkable functional group tolerance. This approach provides a powerful, green, efficient, and facile means to expand the structural diversity of naphtho[2,3-b]furan-4,9-diones and dihydronaph-tho[2,3-b]furan-4,9-diones as promising scaffolds for novel drug discovery.

Keywords

• green chemistry
• photochemistry
• visible-light photocatalysis
• [3+2] cycloaddition
• naphtho[2,3-<i>b</i>]furan-4,9-diones
• dihydronaphtho[2,3-<i>b</i>]furan-4,9-diones