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2025 , Vol. 45 >Issue 1: 307 - 318

DOI: https://doi.org/10.6023/cjoc202405027

研究论文

铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-α]异喹啉酮衍生物

  • 杨梦娜 ,
  • 唐裕才 ,
  • 蒋洁 ,
  • 李佳丽 ,
  • 潘若涵 ,
  • 陈宇 ,
  • 段京林 ,
  • 张松柏
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  • 湖南文理学院化学与材料工程学院 水处理功能材料湖南省重点实验室 电镀废水回用技术湖南省工术研究中心 湖南常德 415000

收稿日期: 2024-05-21

  修回日期: 2024-06-26

  网络出版日期: 2024-07-25

基金资助

湖南省教育厅科学研究基金(23B0650); 湖南省教育厅科学研究基金(23A0503); 湖南省自然科学基金(2022JJ30419); 大学生创新创业训练计划(S202110549001S)

收起

Copper(I)-Catalyzed Acylation/Cyclization of 2-Aryl-N-acryloyl Indole toward Indolo[2,1-α]isoquinoline Derivatives

  • Mengna Yang ,
  • Yucai Tang ,
  • Jie Jiang ,
  • Jiali Li ,
  • Ruohan Pan ,
  • Yu Chen ,
  • Jinglin Duan ,
  • Songbai Zhang
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  • Hunan Provincial Engineering Research Center of Electroplating Wastewater Reuse Technology, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000
*E-mail:

Received date: 2024-05-21

  Revised date: 2024-06-26

  Online published: 2024-07-25

Supported by

Scientific Research Foundation of Hunan Provincial Education Department(23B0650); Scientific Research Foundation of Hunan Provincial Education Department(23A0503); Natural Science Foundation of Hunan Province(2022JJ30419); Innovation and Entrepreneurship Training Program for College Students(S202110549001S)

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摘要

吲哚[2,1-α]异喹啉酮衍生物是一类重要的生物活性分子, 表现出良好的抗菌活性. 发展了一种以CuI为催化剂, 以叔丁基过氧化氢为氧化剂, 以2-芳基吲哚和苯甲酰肼为原料, 实现不饱和双键的自由基酰基化/环化反应构建吲哚[2,1-α]异喹啉酮衍生物的方法. 该方法具有良好的官能团耐受性, 一系列酰基取代的吲哚[2,1-α]异喹啉酮类化合物以中等到良好的收率得到. 自由基捕捉实验表明, 该反应可能经历了自由基历程.

关键词： 吲哚[2,1-α]异喹啉酮; CuI; 2-芳基吲哚; 苯甲酰肼; 酰基化/环化

本文引用格式

杨梦娜 , 唐裕才 , 蒋洁 , 李佳丽 , 潘若涵 , 陈宇 , 段京林 , 张松柏 . 铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-α]异喹啉酮衍生物[J]. 有机化学, 2025 , 45(1) : 307 -318 . DOI: 10.6023/cjoc202405027

Abstract

Indole[2,1-α]isoquinolines are an important class of bioactive molecules and show good antibacterial activity. In the present study, an efficient copper(I)-catalyzed acylation/cyclization has been developed for the construction of indolo[2,1- α]isoquinoline derivatives by utilizing 2-aryl-N-acryloyl indole and benzohydrazide as reactants in the presence of CuI as catalyst and tert-butyl hydroperoxide as oxidant. The present protocol exhibits good functional group tolerance, and a series of acylated indole[2,1-α]isoquinolines were synthesized in moderate to good yields. Radical trapping experiments indicated that the reaction may involve a radical process.

Key words： indolo[2,1-α]isoquinolin-6(5H)-ones; CuI; 2-aryl-N-acryloyl indoles; benzohydrazide; acylation/cyclization

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