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银催化的环化反应合成异喹啉的研究进展
引用本文:牛雁宁,严文轩,张洁,姚应佳,夏晓峰. 银催化的环化反应合成异喹啉的研究进展[J]. 合成化学, 2023, 31(1): 67-81. DOI: 10.15952/j.cnki.cjsc.1005-1511.22066
作者姓名:牛雁宁  严文轩  张洁  姚应佳  夏晓峰
作者单位:1. 南京林业大学 教学科研部,江苏 淮安 223003; 2. 江南大学 化学与材料工程学院 合成与生物胶体教育部重点实验室,江苏 无锡 2142122
基金项目:国家自然科学基金资助项目(22171108); 淮安市自然科学研究计划项目(HAB202065)
摘    要:含有异喹啉骨架的化合物是一类很重要的含氮杂环化合物,广泛存在于具有生物活性的天然产物、有机材料、以及药物分子中。传统的合成异喹啉的方法需要苛刻的反应条件,因此使用温和,简单的方法构建这一骨架的化合物具有重要的现实意义。银类化合物具有路易斯酸特性能够催化活化三键,利用这一特点并使用含氮的亲核试剂进行分子内亲核加成活化的三键是合成异喹啉衍生物的重要方法。本文主要综述了以2-炔基苄亚胺、2-炔基苄基叠氮、2-炔基苯甲醛肟、2-炔基苯甲醛腙及其(2-(乙炔基)芳基)-1,2,3-三唑为反应物,在银催化条件下构建异喹啉环的研究进展,并对部分反应的机理进行了讨论。

关 键 词:银催化剂  异喹啉  亲电环化  合成  机理  炔基  路易斯酸  进展  
收稿时间:2022-04-19

Research Progress on the Synthesis of Isoquinoline viaSilver Catalyzed Cyclization Reaction
NIU Yanning,YAN Wenxuan,ZHANG Jie,YAO Yingjia,XIA Xiaofeng. Research Progress on the Synthesis of Isoquinoline viaSilver Catalyzed Cyclization Reaction[J]. Chinese Journal of Synthetic Chemistry, 2023, 31(1): 67-81. DOI: 10.15952/j.cnki.cjsc.1005-1511.22066
Authors:NIU Yanning  YAN Wenxuan  ZHANG Jie  YAO Yingjia  XIA Xiaofeng
Affiliation:1. Department of Teaching and Research, Nanjing Forestry University, Huai'an 223003, China; 2. Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 2142122, China
Abstract:Isoquinoline skeleton compounds are a very important class of nitrogen-containing heterocyclic compounds. It widely exists in natural products with biological activities, organic materials and drug molecules. The traditional synthesis of isoquinoline requires harsh reaction conditions, so it is very important to construct this skeleton compounds under the mild condition. Silver catalyst can activate three bonds, and further reacts with nitrogen-containing nucleophiles by intramolecular nucleophilic addition, which is an important method for synthesizing isoquinoline derivatives. This paper mainly reviews the latest research progress in the construction of isoquinoline rings with 2-alkynyl benzylimine, 2-alkynyl benzylazide, 2-alkynyl benzaldehyde oxime, 2-alkynyl benzaldehyde hydrazone, and (2-(ethynyl)aryl)-1,2,3-triazoles as reactants via silver catalysis. The mechanism of some reaction was also discussed.
Keywords:silver catalyst  electrophilic cyclization  isoquinoline  synthesis  mechanism  alkynyl  lewis acid  progress  
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