Ni Hangcheng, Mao Hui, Huang Ying, Lu Yi, Liu Zhenxiang
College of Pharmacy, Jinhua Polytechnic, Jinhua 321007, China.
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua 321004, China.
Molecules. 2024 Jun 4;29(11):2649. doi: 10.3390/molecules29112649.
Utilizing iron chloride as a Lewis acid catalyst, we developed a straightforward and mild oxidative cross-coupling reaction between quinoxalinones and indoles, yielding a series of versatile 3-(indol-3-yl)quinoxalin-2-one derivatives. This approach allows for the incorporation of a wide array of functional groups into the final products, demonstrating its synthetic versatility. Notably, the method was successfully scaled up to gram-scale reactions while maintaining high yields. Our mechanistic investigation indicates that iron chloride serves as a catalyst to facilitate the formation of key intermediates which subsequently undergo oxidation to afford the desired products. The merits of this protocol include its cost effectiveness, operational simplicity, and the ease of product isolation via filtration.
我们以氯化铁作为路易斯酸催化剂，开发了一种简单温和的喹喔啉酮与吲哚之间的氧化交叉偶联反应，得到了一系列通用的3-(吲哚-3-基)喹喔啉-2-酮衍生物。这种方法能够将各种各样的官能团引入到最终产物中，展示了其合成的多功能性。值得注意的是，该方法成功放大至克级反应，同时保持了高产率。我们的机理研究表明，氯化铁作为催化剂促进关键中间体的形成，这些中间体随后经过氧化得到所需产物。该方法的优点包括成本效益高、操作简单以及通过过滤易于产物分离。
