Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines

被引：36
|
作者：
Zhao, Ximei [1 ]
Song, Xinlong [1 ]
Jin, Hongming [1 ]
Zeng, Zhongyi [1 ]
Wang, Qian [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构：
[1] Ruprecht Karls Univ Heidelber, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] KAU, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 14期
关键词：
anilines; gold catalysis; heterocycles; quinolones; ynamides; NITRIC-OXIDE SYNTHASE; QUINOLINE DERIVATIVES; CLEAVING ENZYME; RECENT PROGRESS; INHIBITORS; CARBENES; CYCLIZATION; ANTAGONISTS; LIGANDS; POTENT;
D O I：
10.1002/adsc.201800341
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield.
引用
收藏
页码：2720 / 2726
页数：7
相关论文
共 50 条
  • [31] Gold(I)-catalyzed intermolecular (4+2) cycloaddition of allenamides and acyclic dienes
    Faustino, Helio
    Lopez, Fernando
    Castedo, Luis
    Mascarenas, Jose L.
    [J]. CHEMICAL SCIENCE, 2011, 2 (04) : 633 - 637
  • [32] Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals
    Wang, Guanghui
    Jia, Jian
    Liu, Gang
    Yu, Mingwu
    Chu, Xiaoxiao
    Liu, Xiguang
    Zhao, Ximei
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (89) : 11811 - 11814
  • [33] Gold-Catalyzed Intermolecular Enantioselective [2+2] Cycloadditions of Sulfonylallenamides and Styrenes
    Mauleon, Pablo
    [J]. CHEMCATCHEM, 2013, 5 (08) : 2149 - 2151
  • [34] Gold-Catalyzed Intermolecular Nitrene Transfer from 2H-Azirines to Ynamides: A Direct Approach to Polysubstituted Pyrroles
    Zhu, Lei
    Yu, Yinghua
    Mao, Zhifeng
    Huang, Xueliang
    [J]. ORGANIC LETTERS, 2015, 17 (01) : 30 - 33
  • [35] Access to Chiral β-Boryl δ-Lactones via NHC-Catalyzed [4+2] Annulation
    Li, Zhipeng
    Zhang, Jingyang
    Wang, Jian
    [J]. ORGANIC LETTERS, 2024, 26 (09) : 1965 - 1969
  • [36] [2+2] vs. [4+2]: Mechanistic study on gold-catalyzed oxygen transfer of alkynyldiketones and alkynylketoesters
    Liu, Le-Ping
    Malhotra, Deepika
    Hammond, Gerald B.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [37] Gold-Catalyzed Access to Isophosphinoline 2-Oxides
    Hariri, Mina
    Darvish, Fatemeh
    Ndong, Karen-Pacelye Mengue Me
    Sechet, Nora
    Chacktas, Geraud
    Boosaliki, Hooriye
    Do, Minh Loan Tran
    Mwande-Maguene, Gabin
    Lebibi, Jacques
    Burilov, Alexander R.
    Ayad, Tahar
    Virieux, David
    Pirat, Jean-Luc
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7813 - 7824
  • [38] Cobalt-catalyzed domino process for the synthesis of 2-aminoquinolines
    Wang, Jing
    Zhu, Yiwen
    Ying, Jun
    Wu, Xiao-Feng
    [J]. TETRAHEDRON, 2023, 146
  • [39] Regiocontrolled Gold-Catalyzed [2+2+2] Cycloadditions of Ynamides with Two Discrete Nitriles to Construct 4-Aminopyrimidine Cores
    Karad, Somnath Narayan
    Liu, Rai-Shung
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (34) : 9072 - 9076
  • [40] Ligand-Controlled Access to [4+2] and [4+3] Cycloadditions in Gold-Catalyzed Reactions of Allene-Dienes
    Mauleon, Pablo
    Zeldin, Rachel M.
    Gonzalez, Ana Z.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) : 6348 - +
12345