Cu-Catalyzed switchable synthesis of functionalized pyridines and pyrroles

被引:25
|
作者
Ling, Zheng [1 ]
Xie, Fang [1 ]
Gridnev, Ilya D. [2 ]
Terada, Masahiro [2 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn & Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Aramaki 3-6, Sendai, Miyagi 9808578, Japan
基金
中国国家自然科学基金;
关键词
HIGHLY SUBSTITUTED PYRIDINES; DIAZO OXIME ETHERS; MULTICOMPONENT REACTIONS; AMINO-ALCOHOLS; DIELS-ALDER; CYCLOADDITION; REARRANGEMENT; HETEROCYCLES; ACCESS; IMINES;
D O I
10.1039/c8cc05307c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we describe a high yielding and switchable synthesis of a range of functionalized pyridines and pyrroles via Cu-catalyzed cascade reactions with alkynes and N-sulfonyl azadienes which are readily available from saccharin. Both unsymmetrical 2,4,6-trisubstituted pyridines and multi-substituted pyrroles could be transformed into some bioactive compounds and chiral ligands.
引用
收藏
页码:9446 / 9449
页数:4
相关论文
共 50 条
  • [1] Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
    Jiang, Huanfeng
    Yang, Jidan
    Tang, Xiaodong
    Li, Jianxiao
    Wu, Wanqing
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8763 - 8771
  • [2] Cu-catalyzed tandem C-N bond formation for the synthesis of pyrroles and heteroarylpyrroles
    Martin, Ruben
    Larsen, Catharine H.
    Cuenca, Ana
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2007, 9 (17) : 3379 - 3382
  • [3] Regioselective synthesis of highly functionalized alkenylboronates by Cu-catalyzed borylation of propargylic silylalkynes
    Kim, Yeong Eun
    Li, DingXi
    Yun, Jaesook
    DALTON TRANSACTIONS, 2015, 44 (27) : 12091 - 12093
  • [4] Ag-Catalyzed Switchable Synthesis of Site-Specifically Functionalized Pyrroles via Azafulvenium Intermediates
    Yang, Qian-Qian
    Zheng, Ze-Hong
    Wang, Meng
    Zhou, Jin
    Peng, Cheng
    Du, Wei
    Zhan, Gu
    Han, Bo
    ORGANIC LETTERS, 2024, 26 (22) : 4684 - 4689
  • [5] Practical Cu-catalyzed amination of functionalized heteroaryl halides
    Yeh, Vince S. C.
    Wiedeman, Paul E.
    TETRAHEDRON LETTERS, 2006, 47 (34) : 6011 - 6016
  • [6] Synthesis of Pentafluoroethylated Pyridines via Cu-Catalyzed [3+3] Cycloaddition Reaction of Oxime Acetates
    Yang, Siqi
    Li, Xin
    Peng, Zhuojin
    Yu, Wenyan
    Wang, Guangxu
    Jin, Yalan
    Zheng, Bingbing
    Dai, Hongxue
    Bai, Dachang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (06) : 1623 - 1629
  • [7] Indolizine synthesis via Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with nucleophiles
    Liu, Ren-Rong
    Cai, Zheng-Yi
    Lu, Chuan-Jun
    Ye, Shi-Chun
    Xiang, Bin
    Gao, Jianrong
    Jia, Yi-Xia
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (03): : 226 - 230
  • [8] Lewis Acid-Catalyzed Synthesis of Functionalized Pyrroles
    Attanasi, Orazio A.
    Berretta, Stefano
    De Crescentini, Lucia
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 715 - 719
  • [9] Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones
    Zanghi, Joseph M.
    Liu, Shuang
    Meek, Simon J.
    ORGANIC LETTERS, 2019, 21 (13) : 5172 - 5177
  • [10] Cu-Catalyzed Switchable Asymmetric Defluoroalkylation and [3+2] Cycloaddition of Trifluoropropene
    Wang, Hongyi
    Li, Juan
    Peng, Lingzi
    Song, Jin
    Guo, Chang
    ORGANIC LETTERS, 2022, 24 (42) : 7828 - 7833