Divergent Functionalization of N‐Alkyl‐2‐alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines,Chemistry - An Asian Journal

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Divergent Functionalization of N‐Alkyl‐2‐alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-06-10 , DOI: 10.1002/asia.201800441
Jayanta Ghorai ₁ , Angula Chandra Shekar Reddy ₁ , Pazhamalai Anbarasan ₁

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An efficient divergent functionalization of N‐alkylated ortho‐alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium‐catalyzed cross‐dehydrogenative coupling and silver‐mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C−H bond functionalization of 2‐arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.

中文翻译：

N-烷基-2-烯基苯胺的不同功能化：取代的吲哚和喹啉的高效合成

通过分别使用铑催化的交叉脱氢偶联和银介导的氧化环化作用，已实现了N烷基化的邻链烯基苯胺向取代的吲哚和喹啉的高效发散官能化。所开发的方法可耐受各种官能团，并允许以良好至极佳的产率合成取代的吲哚和喹啉。通过转化为具有抗菌活性和2-芳基喹啉CH键功能化的吲哚，可以证明合成效用。此外，在初步的机械研究基础上，提出了一种可行的机制。

更新日期：2018-06-10

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