Dong Yu, Lan Mei-Feng, Lin Yue-Qin, Chen Lin, Wu Chun-Mei, Wang Zhi-Fan, Shi Zhi-Chuan, Deng Guo-Wei, He Bing
College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu 611130, P. R. China.
Southwest Minzu University, Chengdu 610041, P. R. China.
J Org Chem. 2024 May 3;89(9):6474-6488. doi: 10.1021/acs.joc.4c00545. Epub 2024 Apr 12.
We report a step-economic strategy for the direct synthesis of spiro polycyclic N-heterocycles and indolecarbazole-fused naphthoquinones by merging oxidative coupling and cascade palladium-catalyzed intramolecular oxidative cyclization. In the protocol, bi-indolylnaphthoquinones were first synthesized by oxidative coupling of indoles and naphthoquinones. Subsequent cascade palladium-catalyzed intramolecular oxidative cyclization of bi-indolylnaphthoquinones gave spiro polycyclic N-heterocycles and indolecarbazoles. The intramolecular oxidative cyclization approach could also be realized by the presence or absence of iron catalysts under standard conditions. This protocol is featured with moderate to excellent yields, a wide substrate scope, and divergent structures of products.
我们报道了一种通过将氧化偶联与级联钯催化的分子内氧化环化相结合，直接合成螺环多环氮杂环和吲哚咔唑稠合萘醌的步骤经济性策略。在该方案中，首先通过吲哚与萘醌的氧化偶联合成双吲哚基萘醌。随后，双吲哚基萘醌经级联钯催化的分子内氧化环化反应生成螺环多环氮杂环和吲哚咔唑。在标准条件下，分子内氧化环化方法也可通过有无铁催化剂来实现。该方案具有中等至优异的产率、广泛的底物范围和多样的产物结构。
