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银催化的β-芳基-4-戊烯酰胺的串联环化和官能团化:一种合成γ-内酰胺取代醌衍生物的有效途径。

Silver-catalyzed cascade cyclization and functionalization of -aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives.

作者信息

Fang Zeguo, Xie Lin, Wang Liang, Zhang Qian, Li Dong

机构信息

Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology Wuhan 430068 China

New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology Wuhan 430068 China.

出版信息

RSC Adv. 2022 Sep 21;12(41):26776-26780. doi: 10.1039/d2ra05283k. eCollection 2022 Sep 16.

Abstract

The synthesis of γ-lactam-substituted quinone derivatives through a AgO-catalyzed cascade cyclization and functionalization of -aryl-4-pentenamides has been developed. Related 2-oxazolidinone substituted quinone products can be also obtained with -aryl allyl carbamates. The reactions proceed through an amidyl radical-initiated 5--trig cyclization and followed radical addition to quinones. They provide an efficient route to various γ-lactam-substituted quinone derivatives with a wide range of substrate scope.

摘要

通过AgO催化的级联环化反应以及对β-芳基-4-戊烯酰胺的官能团化反应,实现了γ-内酰胺取代的醌衍生物的合成。使用β-芳基烯丙基氨基甲酸酯也可以得到相关的2-恶唑烷酮取代的醌产物。反应通过酰胺基自由基引发的5-exo-trig环化反应,随后是自由基加成到醌上进行。它们为合成具有广泛底物范围的各种γ-内酰胺取代的醌衍生物提供了一条有效途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d89b/9490777/5a4b6c6efdcf/d2ra05283k-f1.jpg

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