Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines  

可见光促进活化烯烃叠氮化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物研究

作　　者：Tang Yucai He Yupeng Yang Biyu Duan Jinglin Du Changyuan Jiang Jie Li Jiali Pan Ruohan Chen Yu Liu Xuewen 唐裕才;何宇鹏;杨碧玉;段京林;杜昌远;蒋洁;李佳丽;潘若涵;陈宇;刘学文(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程技术研究中心,湖南常德415000)

机构地区：[1]Hunan Provincial Key Laboratory of Water Treatment Functional Materials,Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology,College of Chemistry and Materials Engineering,Hunan University of Arts and Science,Changde,Hunan 415000

出　　处：《有机化学》2024年第7期2286-2295,共10页Chinese Journal of Organic Chemistry

基　　金：Project supported by the Scientific Research Foundation of Hunan Provincial Education Department(No.23B0650);the Natural Science Foundation of Hunan Province(No.2022JJ30418);the Key Scientific Research Foundation of Hunan University of Arts and Science(No.22ZD04);the Innovation and Entrepreneurship Training Program for College Students of Hunan University of Arts and Science(No.XDC202318)。

摘　　要：An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide(TMSN3)has been developed using organic dye Rose Bengal as the photocatalyst.This method did not require metal catalysts and additives,and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields.Mechanistic studies demonstrated that the reaction proceeded via a radical pathway.发展了一种以RoseBengal为有机染料光催化剂,在可见光照射下实现2-芳基吲哚与叠氮三甲基硅烷(TMSN3)的自由基叠氮化/环化反应构建叠氮基取代吲哚[2,1-a]异喹啉酮衍生物的方法.该方法无需金属催化剂和添加剂,以空气为氧化剂,以中等到良好的收率得到结构多样的吲哚[2,1-a]异喹啉酮类化合物.机理验证实验表明,该反应经历了自由基历程.

关 键 词：Rose Bengal visible-light 2-aryl indole AZIDATION indolo[2 1-a]isoquinolin-6(5H)-one 

分 类 号：O644.1[理学—物理化学] O626[理学—化学]