Copper-Catalyzed Tandem C-N Bond Formation: An Efficient Annulative Synthesis of Functionalized Cinnolines

被引:61
|
作者
Ball, Catherine J. [1 ]
Gilmore, Jeremy [2 ]
Willis, Michael C. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Eli Lilly & Co Ltd, Lilly Res Ctr, Erl Wood Manor, Windlesham GU20 6PH, Surrey, England
基金
英国工程与自然科学研究理事会;
关键词
annulation; cinnolines; copper catalysis; heterocycles; tandem processes; NITROGEN-HETEROCYCLES; ANTICANCER AGENTS; FACILE SYNTHESIS; DERIVATIVES; ANTIFUNGAL; AMINATION; ALKENYL; LIGANDS; ROUTE;
D O I
10.1002/anie.201201529
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cinn-tillating synthesis: The combination of a readily available copper catalyst, a simple hydrazide nucleophile, and established difunctionalized building blocks provides a new, flexible route to an under-developed class of aromatic heterocycles, cinnolines (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5718 / 5722
页数:5
相关论文
共 50 条
  • [1] Copper-Catalyzed Tandem C-N Bond Formation Reaction: Selective Synthesis of 2-(Trifluoromethyl)benzimidazoles
    Chen, Mu-Wang
    Zhang, Xing-Guo
    Zhong, Ping
    Hu, Mao-Lin
    [J]. SYNTHESIS-STUTTGART, 2009, (09): : 1431 - 1436
  • [2] Synthesis of Dibenzodiazepinones via Tandem Copper(I)-Catalyzed C-N Bond Formation
    Gawande, Sachin D.
    Kavala, Veerababurao
    Zanwar, Manoj R.
    Kuo, Chun-Wei
    Huang, Wen-Chang
    Kuo, Ting-Shen
    Huang, Hsiu-Ni
    He, Chiu-Hui
    Yao, Ching-Fa
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2599 - 2608
  • [3] Copper-Catalyzed Intramolecular C-N Bond Formation: A Straightforward Synthesis of Benzimidazole Derivatives in Water
    Peng, Jinsong
    Ye, Min
    Zong, Cuijuan
    Hu, Fangyun
    Feng, Lingtong
    Wang, Xiaoyan
    Wang, Yufeng
    Chen, Chunxia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 716 - 719
  • [4] Copper-Catalyzed C-N Bond Formation with N-Heterocycles and Aryl Halides
    Boswell, Mikki G.
    Yeung, Fanny G.
    Wolf, Christian
    [J]. SYNLETT, 2012, (08) : 1240 - 1244
  • [5] Contribution to the Mechanism of Copper-Catalyzed C-N and C-O Bond Formation
    Lefevre, Guillaume
    Franc, Gregory
    Tlili, Anis
    Adamo, Carlo
    Taillefer, Marc
    Ciofini, Ilaria
    Jutand, Anny
    [J]. ORGANOMETALLICS, 2012, 31 (22) : 7694 - 7707
  • [6] An efficient synthesis of quinolines via copper-catalyzed C-N cleavage
    Xi, Long-Yi
    Zhang, Ruo-Yi
    Zhang, Lei
    Chen, Shan-Yong
    Yu, Xiao-Qi
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (13) : 3924 - 3930
  • [7] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [8] Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C-N bond formation - Ring-expansion process
    Klapars, A
    Parris, S
    Anderson, KW
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3529 - 3533
  • [9] Synthesis of N-alkyl-N′-aryl-piperazines via copper-catalyzed C-N bond formation
    Yavari, Issa
    Bayat, Mohammad J.
    Ghazanfarpour-Darjani, Majid
    [J]. TETRAHEDRON LETTERS, 2014, 55 (41) : 5595 - 5596
  • [10] Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage
    Xu, Hong-Hui
    Zhang, Xiao-Hong
    Zhang, Xing-Guo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7894 - 7900