Silver-Catalyzed Tandem Radical Cyclization for the Synthesis of 3,3′-Disubstituted Oxindoles

被引:10
作者
Li, Yonghong [1 ]
Wang, Junjiao [1 ]
Wei, Xiaohong [1 ]
Yang, Shangdong [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
silver-catalyzed; radical tandem cyclization; C-H functionalization; carbonyl-containing 3,3 '-disubstituted oxindoles; N-ARYL ACRYLAMIDES; ACTIVATED ALKENES; H ACTIVATION; BOND; DIAMINATION; CASCADE; FUNCTIONALIZATION; AMINOOXYGENATION; EFFICIENT; CARBOCYCLIZATION;
D O I
10.6023/cjoc201412030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new silver-catalyzed oxidative ring opening of cyclopropanols to functionalize alkenes of N-arylacrylamides leading to 3,3'-disubstituted oxindoles has been developed. This reaction is proposed to proceed through oxidative radical ring-opening and C-H functionalization cascade process under the mild reaction conditions with good functional groups tolerance.
引用
收藏
页码:638 / 646
页数:9
相关论文
共 91 条
  • [11] The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization
    Dai, Qiang
    Yu, Jintao
    Jiang, Yan
    Guo, Songjin
    Yang, Haitao
    Cheng, Jiang
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (29) : 3865 - 3867
  • [12] Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes
    Desai, Lopa V.
    Sanford, Melanie S.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) : 5737 - 5740
  • [13] Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations
    Fabry, David C.
    Stodulski, Maciej
    Hoerner, Stefanie
    Gulder, Tanja
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (35) : 10834 - 10838
  • [14] Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides
    Fu, Weijun
    Xu, Fengjuan
    Fu, Yuqin
    Zhu, Mei
    Yu, Jiaqi
    Xu, Chen
    Zou, Dapeng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) : 12202 - 12206
  • [15] Conversion of acid chloride into homoallylic alcohol via allylic C-H bond activation of alkene with a zirconocene complex
    Fujita, K
    Yorimitsu, H
    Shinokubo, H
    Matsubara, S
    Oshima, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 12115 - 12116
  • [16] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    Galliford, Chris V.
    Scheidt, Karl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758
  • [17] Copper-catalyzed oxidative cascade coupling of N-alkyl-N-phenylacrylamides with aryl aldehydes
    Gong, Weiwei
    Xu, Lei
    Ji, Tao
    Xie, Ping
    Qi, Xueyong
    Pittman, Charles U., Jr.
    Zhou, Aihua
    [J]. RSC ADVANCES, 2014, 4 (13): : 6854 - 6857
  • [18] Trifluoroacetic Acid-Promoted Synthesis of 3-Hydroxy, 3-Amino and Spirooxindoles from α-Keto-N-Anilides
    Gorokhovik, Ioulia
    Neuville, Luc
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5536 - 5539
  • [19] An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes
    Iglesias, Alvaro
    Perez, Edwin G.
    Muniz, Kilian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8109 - 8111
  • [20] γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C-H Activation of Quinones Using Cyclopropanols
    Ilangovan, Andivelu
    Saravanakumar, Shanmugasundar
    Malayappasamy, Subramani
    [J]. ORGANIC LETTERS, 2013, 15 (19) : 4968 - 4971