Transition-Metal-Mediated/Catalyzed Synthesis of Pyridines, Pyrimidines, and Triazines by [2+2+2] Cycloaddition Reactions

被引:48
作者
Nagata, Tatsuki [1 ]
Obora, Yasushi [1 ]
机构
[1] Kansai Univ, Dept Chem & Mat Engn, Suita, Osaka 5648680, Japan
关键词
Cycloaddition; Pyridine; Pyrimidine; Triazine; Nitrogen heterocycles; ONE-POT SYNTHESIS; IRON-CATALYZED CYCLOADDITION; 2 DIFFERENT ALKYNES; SUBSTITUTED PYRIDINES; CASCADE ANNULATION; PROMISING SCAFFOLD; NITRILES; DIYNES; DERIVATIVES; CYCLOTRIMERIZATION;
D O I
10.1002/ajoc.202000240
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen-containing six-membered heterocycles such as pyridines, pyrimidines, and triazines are widely used in the synthesis of natural products and pharmaceuticals. Recently, a promising approach to these structures via [2+2+2] cycloadditions of alkynes and nitriles has been developed. Transition-metal complex catalysts play key roles in the regio-, chemo-, or stereo-selectivity of transformations. Here, we summarize recent advances in metal-mediated/catalyzed [2+2+2] cycloadditions for synthesizing pyridines and pyrimidines. We also describe progress in triazine synthesis via metal-mediated/catalyzed nitrile cyclotrimerization.
引用
收藏
页码:1532 / 1547
页数:16
相关论文
共 89 条
  • [1] Recent Advances in Stereoselective [2+2+2] Cycloadditions
    Amatore, Muriel
    Aubert, Corinne
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) : 265 - 286
  • [2] Highly Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Diynes to Sulfonimines
    Amatore, Muriel
    Leboeuf, David
    Malacria, Max
    Gandon, Vincent
    Aubert, Corinne
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) : 4576 - 4579
  • [3] [Anonymous], 2017, ANGEW CHEM, V129, P4902
  • [4] [Anonymous], 2014, ANGEW CHEM, V126, P9218
  • [5] [Anonymous], 2011, ANGEW CHEM, V123, P7300
  • [6] [Anonymous], COMPREHENSIVE ORGANI, P2241
  • [7] [Anonymous], 2013, ANGEW CHEM, V125, P5431
  • [9] New symmetrically substituted 1,3,5-triazines as host compounds for channel-type inclusion formation
    Berger, Ricarda
    Hauser, Juerg
    Labat, Gael
    Weber, Edwin
    Hulliger, Juerg
    [J]. CRYSTENGCOMM, 2012, 14 (03): : 768 - 770
  • [10] Additive-Controlled Switchable Selectivity from Cyanobenzenes to 2-Alkynylpyridines: Ruthenium(II)-Catalyzed [2+2+2] Cycloadditions of Diynes and Alkynylnitriles
    Bhatt, Divya
    Patel, Neha
    Chowdhury, Hrishikesh
    Bharatam, Prasad V.
    Goswami, Avijit
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (09) : 1876 - 1882