Metal-Free [2+2+2] Cycloaddition of Ynamides with Nitriles to Construct 2,4-Diaminopyridines

被引:42
|
作者
Zhang, Jingyi
Zhang, Qingshuang
Xia, Biao
Wu, Jie
Wang, Xiao-Na [1 ]
Chang, Junbiao [1 ]
机构
[1] Zhengzhou Univ, Sch Pharmaceut Sci, Collaborat Innovat Ctr New Drug Res & Safety Eval, Henan Prov, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
N BOND-CLEAVAGE; IRON-CATALYZED CYCLOADDITION; ROOM-TEMPERATURE; PYRIDINES; DIYNES; CYCLOTRIMERIZATION; CYANAMIDES; YNAMINES; ALKYNES; HETEROCYCLES;
D O I
10.1021/acs.orglett.6b01546
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a metal-free [2 + 2 + 2] cyclo-addition of ynamides with nitriles that enables highly efficient access to 2,4-diaminopyridines. This catalytic protocol is more environmentally friendly and allows for a concomitant construction of C-C and C-N bonds between ynamides and nitriles, exhibiting excellent chemoselectivity, regioselectivity, and wide functional groups tolerance.
引用
收藏
页码:3390 / 3393
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
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9704 - 9708
  • [2] 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
    ORGANIC LETTERS, 2019, 21 (05) : 1331 - 1336
  • [3] Sulfonamide-directed gold-catalyzed [2+2+2]-cycloadditions of nitriles with two discrete ynamides to construct 2,4-diaminopyridine cores
    Chen, Yu-Ling
    Sharma, Pankaj
    Liu, Rai-Shung
    CHEMICAL COMMUNICATIONS, 2016, 52 (15) : 3187 - 3190
  • [4] Transition metal-free formal [2+2+2] cycloaddition reactions of alkynes
    Hapke, Marko
    TETRAHEDRON LETTERS, 2016, 57 (51) : 5719 - 5729
  • [5] Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions
    Xie, Lan-Gui
    Shaaban, Saad
    Chen, Xiangyu
    Maulide, Nuno
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (41) : 12864 - 12867
  • [6] Regiocontrolled Gold-Catalyzed [2+2+2] Cycloadditions of Ynamides with Two Discrete Nitriles to Construct 4-Aminopyrimidine Cores
    Karad, Somnath Narayan
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (34) : 9072 - 9076
  • [7] Metal-Free [3+2] Annulation of Ynamides with Anthranils to Construct 2-Aminoindoles
    Zhang, Jingyi
    Li, Ying
    Zhang, Chaofeng
    Wang, Xiao-Na
    Chang, Junbiao
    ORGANIC LETTERS, 2021, 23 (06) : 2029 - 2035
  • [8] Synthesis of Tricyclic Fused 3-Aminopyridines through Intramolecular CoI-Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes
    Garcia, Pierre
    Moulin, Solenne
    Miclo, Yves
    Leboeuf, David
    Gandon, Vincent
    Aubert, Corinne
    Malacria, Max
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2129 - 2139
  • [9] Ruthenium-Catalyzed [2+2+2] Cycloaddition of ,-Diynes and Selenocyanates: An Entry to Selenopyridine Derivatives
    Tran, Christine
    Haddad, Mansour
    Ratovelomanana-Vidal, Virginie
    SYNTHESIS-STUTTGART, 2019, 51 (12): : 2532 - 2541
  • [10] Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2+2+2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes
    Wang, Gaonan
    You, Xu
    Gan, Yi
    Liu, Yuanhong
    ORGANIC LETTERS, 2017, 19 (01) : 110 - 113