Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines

作者：Jiahui Zhang, Yang‐Yang Hu, Ya’nan Ran, Huiying Liu, Jing‐Wen Sun, Haijun Wang, Lei Liu · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.4c02375 · 被引用次数：4 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions

A novel [3+3] cyclization reaction between phenol and hydrazone was successfully developed under electrochemically driven conditions. This reaction provided access to a diverse array of 1,3,4-oxadiazinane compounds in consistently high yields, reaching up to 87%. Notably, the reaction exhibited remarkable tolerance toward a broad spectrum of both phenol and hydrazone substrates, underscoring its versatility. Moreover, the protocol distinguished itself by its exceptional atom and step economy, facilitating the efficient construction of functionalized 1,3,4-oxadiazines. The synthetic utility of this approach was further exemplified by its scalability, as demonstrated by gram-scale reactions, and its broad substrate scope.