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芳基磺酰化引发的3-烯基吲哚环化反应用于合成四氢-γ-咔啉

Arylsulfonylation-Triggered Cyclization of 3-Alkenyl Indoles Enabling Synthesis of Tetrahydro-γ-carboline.

作者信息

Liu Aiyao, He Jingrui, Yu Yingjie, Wang Chengting, Mei Haibo, Han Jianlin

机构信息

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

出版信息

J Org Chem. 2022 Sep 2;87(17):11469-11477. doi: 10.1021/acs.joc.2c01033. Epub 2022 Aug 15.

DOI:10.1021/acs.joc.2c01033
PMID:35969019
Abstract

A visible-light promoted cyclization reaction of 3-alkenyl indole derivatives with arylsulfonyl chlorides as coupling partners has been developed, which afforded functionalized tetrahydro-γ-carbolines in good chemical yields. The reaction used 3-alkenyl indoles as radical acceptors and proceeded via the sequence of sulfonylation and intramolecular cyclization. The reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides an efficient strategy for the synthesis of tetrahydro-γ-carboline derivatives.

摘要

已开发出一种可见光促进的3-烯基吲哚衍生物与芳基磺酰氯作为偶联伙伴的环化反应,该反应能以良好的化学产率得到功能化的四氢-γ-咔啉。该反应使用3-烯基吲哚作为自由基受体,通过磺酰化和分子内环化的顺序进行。该反应在温和条件下进行,并且能耐受多种底物,这为四氢-γ-咔啉衍生物的合成提供了一种有效的策略。

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