湖北师范大学殷国栋团队实现了通过C2原子的重新分布重塑吲哚环：可切换地获得菲啶和菲啶氮氧化物。2025年7月9日出版的《中国化学》杂志发表了这项成果。

研究组通过断裂硝基联苯吲哚的C₂–N₁键并实现C₂原子重新分配，完成了其骨架重构。通过精确调控盐酸用量和反应气氛，可切换地合成了多种菲啶（phenanthridines）和菲啶N-氧化物（phenanthridine N-oxides）。放大合成与产物的后期修饰拓展了该方法的应用潜力。密度泛函理论（DFT）计算表明，吲哚环的开环需要乙醇（EtOH）参与。该研究为氮杂环骨架的重构与转化建立了理想平台。

附：英文原文

Title: Remodeling of the Indole Ring with Redistribution of the C2 Atom: Switchable Access to Phenanthridines and Phenanthridine N-Oxides

Author: Li Yang, Cheng Xu, Zheng Liu, Lijing Zhong, Qing Wang, Qian Shu, Shui Qian, Rongchuan Su, Guodong Yin, Ge Gao

Issue&Volume: 2025-07-09

Abstract: The skeletal remodeling of nitro-biphenyl indoles has been achieved via the cleavage of C2–N1 bond of and redistribution of the C2 atom. A diverse range of phenanthridines and phenanthridine N-oxides were switchably synthesized through fine-tuning the amount of HCl and reaction atmosphere. The scale-up synthesis and late-stage modification of the resulting products expand the application potential of this methodology. Furthermore, DFT calculations indicate that the ring-opening of indole necessitates the assistance of EtOH. This work establishes an attractive platform for the remodeling and conversion of N-heterocyclic frameworks.

DOI: 10.1002/cjoc.70168

Source: https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70168