Rhodium-Catalyzed C(sp 2 )–H Activation and [3+3] Annulation: Accessing Pyrano[3,2- c ]chromene-2,5-diones as TASK-3 Activators

作者：Xueqing Liu, Shuoshuo Zheng, Qingjie Ge, Tian Cao, Fanqi Zeng, Fuyun Tian, Zhiyue He, Zhaobing Gao, Xiaowei Wu · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c00011 · 被引用次数：11 · 研究领域：Catalytic C–H Functionalization Methods、Synthesis and Catalytic Reactions、Cyclopropane Reaction Mechanisms

Herein, an efficient Rh-catalyzed C–H activation/annulation between α,β-unsaturated amides and coumarin-derived iodonium ylides has been developed, affording novel pyrano[3,2- c ]chromene-2,5-diones and analogues in high yields. Most products could be easily isolated by precipitation in ethanol, followed by simple filtration. Additionally, this protocol demonstrated the benefits of environmentally friendly conditions, air compatibility, good functional group compatibility, scale-up synthesis with low catalyst loading, and a recyclable Rh catalyst. Importantly, compounds 3m and 3w demonstrated moderate agonist activity on the TASK-3 channel, with I / I 0 values of 1.7650 ± 0.1058 and 1.400 ± 0.0589, respectively.