Facile Synthesis of Azaarene-Substituted 3-Hydroxy-2-oxindoles via Bronsted Acid Catalyzed sp3 C-H Functionalization

被引：142
|
作者：
Niu, Rui [1 ,2 ,3 ]
Xiao, Jian [1 ]
Liang, Tao [1 ]
Li, Xingwei [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Ocean Univ China, Coll Environm Sci & Engn, Qingdao 266100, Peoples R China
[3] Ocean Univ China, Minist Educ, Key Lab Marine Environm & Ecol, Qingdao 266100, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 03期
基金：
中国国家自然科学基金;
关键词：
BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYSIS; ISATIN DERIVATIVES; BOND ACTIVATION; 3-HYDROXYOXINDOLE DERIVATIVES; ARYLBORONIC ACIDS; ALPHA-KETOAMIDES; ALDOL REACTION; OXINDOLES;
D O I：
10.1021/ol2030982
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bronsted acid catalyzed functionalization of sp(3) C-H bonds in 2-methyl azaarenes has been achieved in the reaction with isatins. This method provides facile synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step in moderate to good yields.
引用
收藏
页码：676 / 679
页数：4
相关论文
共 50 条
  • [41] Iridium-catalyzed sp3 C-H Alkylation of 3-Carbonyl-2-(alkylamino)pyridines with Alkenes
    Nagai, Masaki
    Nagamoto, Midori
    Nishimura, Takahiro
    Yorimitsu, Hideki
    CHEMISTRY LETTERS, 2017, 46 (08) : 1176 - 1178
  • [42] Chiral phosphine-squaramide-catalyzed Morita-Baylis-Hillman reaction: enantioselective synthesis of 3-hydroxy-2-oxindoles
    Qian, Jing-Ying
    Wang, Ci-Ci
    Sha, Feng
    Wu, Xin-Yan
    RSC ADVANCES, 2012, 2 (14) : 6042 - 6048
  • [43] Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C-C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides
    Wang, Junwei
    Yuan, Yucheng
    Xiong, Rui
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ORGANIC LETTERS, 2012, 14 (09) : 2210 - 2213
  • [44] Functionalization of Tetraorganosilanes and Permethyloligosilanes at a Methyl Group on Silicon via Iridium-Catalyzed C(sp3)-H Borylation
    Ohmura, Toshimichi
    Torigoe, Takeru
    Suginome, Michinori
    ORGANOMETALLICS, 2013, 32 (21) : 6170 - 6173
  • [45] Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation
    Chen, Chao
    Xu, Xiu-Hua
    Yang, Bin
    Qing, Feng-Ling
    ORGANIC LETTERS, 2014, 16 (12) : 3372 - 3375
  • [46] iEDDA Reaction of the Molecular Iodine-Catalyzed Synthesis of 1,3,5-Triazines via Functionalization of the sp3 C-H Bond of Acetophenones with Amidines: An Experimental Investigation and DFT Study
    Tiwari, Abhishek R.
    Nath, Shilpa R.
    Joshi, Kaustubh A.
    Bhanage, Bhalchandra M.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) : 13239 - 13249
  • [47] Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins
    Yan, Tingting
    Wang, Xiaoyan
    Sun, Hongbao
    Liu, Jie
    Xie, Yongmei
    MOLECULES, 2013, 18 (12) : 14505 - 14518
  • [48] Synthesis of α-Quaternary β-Lactams via Copper-Catalyzed Enantioconvergent Radical C(sp3)-C(sp2) Cross-Coupling with Organoboronate Esters
    Wang, Fu-Li
    Liu, Lin
    Yang, Chang-Jiang
    Luan, Cheng
    Yang, Jing
    Chen, Ji-Jun
    Gu, Qiang-Shuai
    Li, Zhong-Liang
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)
  • [49] CuI-amidobis(phosphine) catalyzed C(sp3)-C(sp3) direct homo- and hetero-coupling of unactivated alkanes via C(sp3)-H activation
    Sonawane, Sachin C.
    Gourkhede, Rani
    Saini, Prateek
    Ramakrishnan, Srinivasan
    Balakrishna, Maravanji S.
    CHEMICAL COMMUNICATIONS, 2024, 60 (47) : 6055 - 6058
  • [50] Hydroxoiridium-Catalyzed sp3 C-H Alkylation of Indoline Derivatives with Terminal Alkenes
    Nakamura, Ikumi
    Yamauchi, Daisuke
    Nishimura, Takahiro
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1347 - 1350
12345