Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

被引：83
|
作者：
Xie, Lan-Gui [1 ]
Shaaban, Saad [1 ]
Chen, Xiangyu [1 ]
Maulide, Nuno [1 ]
机构：
[1] Univ Vienna, Inst Organ Chem, Wahringer Str 38, A-1090 Vienna, Austria
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 41期
关键词：
alkynes; cycloaddition; heteroalkynes; nitriles; pyridines; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; DE-NOVO SYNTHESIS; FUNCTIONALIZED PYRIDINES; REGIOSELECTIVE SYNTHESIS; CATALYZED CYCLOADDITION; INTERNAL THIOALKYNES; VINYL AZIDES; CYCLOTRIMERIZATION; NITRILES;
D O I：
10.1002/anie.201606604
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A BrOnsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.
引用
收藏
页码：12864 / 12867
页数：4
相关论文
共 50 条
  • [1] Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines
    Wang, Yong
    Song, Li-Juan
    Zhang, Xinhao
    Sun, Jianwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9704 - 9708
  • [2] Transition metal-free formal [2+2+2] cycloaddition reactions of alkynes
    Hapke, Marko
    [J]. TETRAHEDRON LETTERS, 2016, 57 (51) : 5719 - 5729
  • [3] Photocatalyzed [2+2+2]-cycloaddition of nitriles with acetylene: An effective method for the synthesis of 2-pyridines under mild conditions
    Heller, B
    Sundermann, B
    Buschmann, H
    Drexler, HJ
    You, JS
    Holzgrabe, U
    Heller, E
    Oehme, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13): : 4414 - 4422
  • [4] Metal-free synthesis of highly substituted quinolines under mild conditions
    Natarajan, Rakesh
    Unnikrishnan, Peruparambil A.
    Radhamani, Sandhya
    Rappai, John P.
    Prathapan, Sreedharan
    [J]. TETRAHEDRON LETTERS, 2016, 57 (27-28) : 2981 - 2984
  • [5] Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition
    Raimondi, Wilfried
    Dauzonne, Daniel
    Constantieux, Thierry
    Bonne, Damien
    Rodriguez, Jean
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (31) : 6119 - 6123
  • [6] RHODIUM-CATALYZED [2+2+2] CYCLOADDITION FOR THE SYNTHESIS OF SUBSTITUTED PYRIDINES, PYRIDONES, AND THIOPYRANIMINES
    Tanaka, Ken
    [J]. HETEROCYCLES, 2012, 85 (05) : 1017 - 1043
  • [7] Synthesis of Amino-Substituted α- and δ-Carbolines via Metal-Free [2+2+2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides
    Zhang, Jingyi
    Guo, Meichao
    Chen, Yajuan
    Zhang, Shuangshuang
    Wang, Xiao-Na
    Chang, Junbiao
    [J]. ORGANIC LETTERS, 2019, 21 (05) : 1331 - 1336
  • [8] Metal-Free [2+2+2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives
    Wen, Hao
    Cao, Wei
    Liu, Yu
    Wang, Liang
    Chen, Ping
    Tang, Yu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13308 - 13324
  • [9] Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions
    Xuan, Jun
    Xia, Xu-Dong
    Zeng, Ting-Ting
    Feng, Zhu-Jia
    Chen, Jia-Rong
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5653 - 5656
  • [10] Recent Advances in the Synthesis of Pyridines by Transition-Metal-Catalyzed [2+2+2] Cycloaddition
    Varela, Jesus A.
    Saa, Carlos
    [J]. SYNLETT, 2008, (17) : 2571 - 2578
12345