硝基苯
化学
环加成
戒指(化学)
苯
卡宾
催化作用
药物化学
劈理(地质)
立体化学
光化学
有机化学
岩土工程
断裂(地质)
工程类
作者
Kai‐Jie Wei,Menglu Jiang,Siyu Liang,Wei Yu
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2022-08-02
卷期号:54 (23): 5203-5214
被引量:3
摘要
Abstract Nitrenoid-mediated C–H insertion and cycloaddition reactions are gaining increasing importance in modern organic synthesis. However, the nitrene-mediated benzene ring expansion, which constitutes a potent tool for breaking the benzene ring, has sparely been explored for synthetic purposes. Herein we report that nitrene cycloaddition to the benzene ring can be enabled intramolecularly by iron catalysis. By using FeCl2 and N-heterocyclic carbene SIPr·HCl as the catalyst, α-azido-N-phenylamides can be converted into 1,3-dihydro-2H-azepin-2-ones in good yields through a novel skeleton rearrangement. The rearrangement features a cascade of nitrene cycloaddition, C–N cleavage, water addition, and electrocyclic ring-opening. In the case that the N-phenyl ring is substituted with a methoxy group at the meta or para position, azepin-2-one-fused imidazolinones can also be obtained. The present reactions provide an effective method for benzene ring expansion as well as for the preparation of azepin-2-one compounds.
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