Progress in Synthesis of Oxindoles by Radical Addition-Cyclization

被引:35
作者
Mai, Wenpeng [1 ]
Wang, Jitao [1 ]
Yang, Liangru [1 ]
Yan, Jinwei [1 ]
Mao, Pu [1 ]
Xiao, Yongmei [1 ]
Qu, Lingbo [1 ]
机构
[1] Henan Univ Technol, Sch Chem & Chem Engn, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
transition metal; metal-free; photoredox catalysis; oxindoles; PLATELET AGGREGATION INHIBITORS; H FUNCTIONALIZATION CASCADE; N-ARYL ACRYLAMIDES; ACTIVATED ALKENES; 2-OXOQUINOLINE DERIVATIVES; BIOLOGICAL-ACTIVITIES; BOND; TRIFLUOROMETHYLATION; CARBOCYCLIZATION; ARYLACRYLAMIDES;
D O I
10.6023/cjoc201405006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In recent years, there are many reports about the synthesis of oxindoles by radical addition-cyclization. Most of these approaches are catalyzed by different transition metals, or under metal-free and photoredox catalysis conditions using N-arylacrylamides as main substrates. These methods have been a powerful strategy to obtain oxindoles in organic synthesis. At present, the studies on the synthesis of oxindoles by radical addition-cyclization are mainly focused on the types of radicals and the reaction mechanisms. This review will summarize the recent progress of the synthesis of oxindoles by radical addition-cyclization according to the different catalyst systems.
引用
收藏
页码:1958 / 1965
页数:8
相关论文
共 51 条
  • [1] 2(1H)-QUINOLINONES WITH CARDIAC STIMULANT ACTIVITY .2. SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 6-(N-LINKED, 5-MEMBERED HETEROARYL) DERIVATIVES
    ALABASTER, CT
    BELL, AS
    CAMPBELL, SF
    ELLIS, P
    HENDERSON, CG
    MORRIS, DS
    ROBERTS, DA
    RUDDOCK, KS
    SAMUELS, GMR
    STEFANIAK, MH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) : 575 - 583
  • [2] 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
  • [3] 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
  • [4] NOVEL POSITIVE INOTROPIC AGENTS - SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 6-(3-AMINO-2-HYDROXYPROPOXY)-2(1H)-QUINOLINONE DERIVATIVES
    FUJIOKA, T
    TERAMOTO, S
    MORI, T
    HOSOKAWA, T
    SUMIDA, T
    TOMINAGA, M
    YABUUCHI, Y
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (20) : 3607 - 3612
  • [5] Catalysis for fluorination and trifluoromethylation
    Furuya, Takeru
    Kamlet, Adam S.
    Ritter, Tobias
    [J]. NATURE, 2011, 473 (7348) : 470 - 477
  • [6] Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles
    Jaegli, Stephanie
    Dufour, Jeremy
    Wei, Hai-long
    Piou, Tiffany
    Duan, Xin-Hua
    Vors, Jean-Pierre
    Neuville, Luc
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2010, 12 (20) : 4498 - 4501
  • [7] Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles
    Li, Lei
    Deng, Min
    Zheng, Sheng-Cai
    Xiong, Ya-Ping
    Tan, Bin
    Liu, Xin-Yuan
    [J]. ORGANIC LETTERS, 2014, 16 (02) : 504 - 507
  • [8] Synthesis of Sulfonated Oxindoles by Potassium Iodide Catalyzed Arylsulfonylation of Activated Alkenes with Sulfonylhydrazides in Water
    Li, Xiaoqing
    Xu, Xiangsheng
    Hu, Peizhu
    Xiao, Xuqiong
    Zhou, Can
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) : 7343 - 7348
  • [9] Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc
    Li, Ya-Min
    Shen, Yuehai
    Chang, Kwen-Jen
    Yang, Shang-Dong
    [J]. TETRAHEDRON LETTERS, 2014, 55 (13) : 2119 - 2122
  • [10] Metal-free oxidative arylphosphination of activated N-substituted-N-arylacrylamide derivatives using K2S2O8
    Li, Ya-Min
    Shen, Yuehai
    Chang, Kwen-Jen
    Yang, Shang-Dong
    [J]. TETRAHEDRON, 2014, 70 (11) : 1991 - 1996