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An Efficient Synthesis of Naphtho[2,3-b]furan-4,9-diones via Visible-Light-Mediated [3+2] Cycloaddition Reaction. 2023

Hongbo Tan, and Zehui Qi, and Yuanhui Yu, and Xu Zhang, and Yuheng Xiang, and Jingwen Huang, and Zhigang Xu, and Dianyong Tang, and Zhongzhu Chen, and Bochu Wang
National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Engineering Laboratory of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators as Innovative Medicine, Chongqing Collaborative Innovation Center of Targeted and Innovative Therapeutics, College of Pharmacy & IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.

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.

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