Cp*CoIII-Catalyzed C(7)-H Bond Annulation of Indolines with Alkynes

被引：23
|
作者：
Mandal, Rajib [1 ]
Garai, Bholanath [1 ]
Sundararaju, Basker [1 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Fine Chem Lab, Kanpur 208016, Uttar Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 14期
关键词：
N-CARBAMOYL INDOLINES; H AMIDATION; COBALT(III)-CATALYZED SYNTHESIS; CARBON-HYDROGEN; INDOLES; ARENES; FUNCTIONALIZATION; INTERMEDIATE; ALKENYLATION; DERIVATIVES;
D O I：
10.1021/acs.joc.1c00713
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the synthesis of biologically essential pyrroloquinolinones has been developed under Cp*Co-III in catalysis, which involves a cascade reaction of C(7)-H alkenylation with alkynes followed by nucleophilic addition. A wide variety of internal alkynes including enyne, diyne, and ynamide and more challenging terminal alkynes were successfully employed for the annulation in good to excellent yield with high regioselectivity.
引用
收藏
页码：9407 / 9417
页数：11
相关论文
共 50 条
  • [31] Iridium( I)-Catalyzed Direct C-H Bond Alkylation of the C-7 Position of Indolines with Alkenes
    Pan, Shiguang
    Ryu, Naoto
    Shibata, Takanori
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) : 929 - 933
  • [32] CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C-H and N-H bonds of Arylamides
    Kalsi, Deepti
    Barsu, Nagaraju
    Sundararaju, Basker
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (10) : 2360 - 2364
  • [33] Cobalt(II)-Catalyzed [4+2] Annulation of Picolinamides with Alkynes via C-H Bond Activation
    Yao, Yongqi
    Lin, Qifu
    Yang, Wen
    Yang, Weitao
    Gu, Fenglong
    Guo, Wei
    Yang, Dingqiao
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (25) : 5607 - 5610
  • [34] Cooperative Lewis Acid/Cp*CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones
    Kim, Ju Hyun
    Gressies, Steffen
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) : 5577 - 5581
  • [35] Electrochemical Rhodium-Catalyzed Enantioselective C-H Annulation with Alkynes
    Huang, Yuan-Qiong
    Wu, Zhi-Jie
    Zhu, Li
    Gu, Qing
    Lu, Xiaojie
    You, Shu-Li
    Mei, Tian-Sheng
    CCS CHEMISTRY, 2022, 4 (09): : 3181 - 3189
  • [36] Ruthenium(II)-Catalyzed C-H Bond [3+2] Annulation of N-Nitrosoanilines with Alkynes in Water
    Chen, Xun
    Cui, Xue
    Bai, Lili
    Wang, Ying
    Xie, Ying
    Wang, Shuojin
    Zhai, Ruirui
    Zhao, Ke
    Kong, Dulin
    Li, Youbin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (12) : 2209 - 2212
  • [37] Rhodium(III)-Catalyzed Oxidative Annulation of 7-Azaindoles and Alkynes via Double C-H Activation
    Li, Shuai-Shuai
    Wang, Cheng-Qi
    Lin, Hui
    Zhang, Xiao-Mei
    Dong, Lin
    ORGANIC LETTERS, 2015, 17 (12) : 3018 - 3021
  • [38] Cp*CoIII-catalyzed formal [4+2] cycloaddition of 2-phenyl-1H-imidazoles to afford imidazo[1,2-c]quinazoline derivatives
    Wu, Deyu
    Liu, Zhengqiang
    Chang, Yiting
    Chen, Jiajing
    Qi, Haixiang
    Dong, Yi
    Xu, Heng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (24) : 4993 - 4998
  • [39] Cp*CoIII Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks
    Bera, Sourav Sekhar
    Debbarma, Suvankar
    Ghosh, Avick Kumar
    Chand, Santanu
    Maji, Modhu Sudan
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 420 - 430
  • [40] Divergent rhodium-catalyzed electrochemical vinylic C–H annulation of acrylamides with alkynes
    Yi-Kang Xing
    Xin-Ran Chen
    Qi-Liang Yang
    Shuo-Qing Zhang
    Hai-Ming Guo
    Xin Hong
    Tian-Sheng Mei
    Nature Communications, 12
12345