Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones

被引:66
|
作者
Suzuki, Yamato [1 ]
Naoe, Saori [1 ]
Oishi, Shinya [1 ]
Fujii, Nobutaka [1 ]
Ohno, Hiroaki [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
关键词
ONE-POT; FACILE SYNTHESIS; AMINES; ACCESS; CYCLIZATION; PYRAZOLES; HYDROAMINATION; ADDITIONS; BONDS;
D O I
10.1021/ol203072u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroamination. Cascade cyclization using 1,2-dialkynylbenzene derivatives as the alkyne component was also performed producing fused tricyclic dihydropyrazoles in good yields.
引用
收藏
页码:326 / 329
页数:4
相关论文
共 50 条
  • [31] Three-Component Reactions of Aldehydes, Amines, and Alkynes/Alkenes Catalyzed by Trifluoromethanesulfonic Acid: An Efficient Route to Substituted Quinolines
    Zhang, Xu
    Xu, Xuefeng
    Yu, Lintao
    Zhao, Qiang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (03) : 281 - 284
  • [32] Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates
    Yu, Congjun
    Ma, Xiaodong
    Chen, Bin
    Tang, Bencan
    Paton, Robert S.
    Zhang, Guozhu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (11) : 1561 - 1565
  • [33] Copper(II) Triflate-Catalyzed Three-Component Coupling of Aldehydes, Alkynes and Carbamates
    Dou, Xiao-Yong
    Qi Shuai
    He, Liang-Nian
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2437 - 2440
  • [34] Three-Component Coupling of Aldehydes, Amines, and Alkynes Catalyzed by Oxidized Copper Nanoparticles on Titania
    Jose Albaladejo, Maria
    Alonso, Francisco
    Moglie, Yanina
    Yus, Miguel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (16) : 3093 - 3104
  • [35] SYNTHESIS OF PYRAZOLES THROUGH COPPER-CATALYZED THREE-COMPONENT COUPLING OF ALDEHYDES, ALKYNES, AND p-TOLUENESULFONYLHYDRAZIDE
    Wu, Feng
    Hao, Lu
    Zhan, Zhuang-ping
    HETEROCYCLES, 2013, 87 (03) : 657 - 663
  • [36] Synthesis of Propargylamines by Three-Component Coupling of Aldehydes, Amines and Alkynes Catalyzed by Magnetically Separable Copper Ferrite Nanoparticles
    Kantam, M. Lakshmi
    Yadav, Jagjit
    Laha, Soumi
    Jha, Shailendra
    SYNLETT, 2009, (11) : 1791 - 1794
  • [37] Three-Component Synthesis of Di-Keto Aziridines and Highly Functionalized Alkenes from Sulfoxonium Ylides, Nitrosoarenes, and Alkynes
    Zhai, Pingan
    Fang, Yongsheng
    Li, Wenhui
    Lin, Jianying
    Li, Xing
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12194 - 12207
  • [38] 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
  • [39] Copper(II)-Catalyzed Three-Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes: A Regioselective Synthesis of Multiply Substituted Quinolines
    Wang, Yong
    Chen, Chao
    Peng, Jing
    Li, Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) : 5323 - 5327
  • [40] Highly efficient allylation of aldehydes and three-component synthesis of homoallylamines using bismuth triflate catalyst
    Choudary, BM
    Chidara, S
    Sekhar, CVR
    SYNLETT, 2002, (10) : 1694 - 1696