A simple and eco-friendly method for the aminomethylation of 3-substituted oxindoles via three-component Mannich reaction in aqueous media

被引:23
作者
Liu, Xiong-Li [1 ,2 ]
Zhang, Xiao-Mei [1 ]
Yuan, Wei-Cheng [1 ]
机构
[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
Oxindole; Mannich reaction; Formalin; Aminomethylation; Water mediated reaction; ALDOL-TYPE REACTION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PROCHIRAL NUCLEOPHILES; ASYMMETRIC MICHAEL; ALLYLIC ALKYLATION; QUATERNARY CARBON; ISATINS; 2-OXINDOLES; CATALYSTS;
D O I
10.1016/j.tetlet.2010.12.060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and eco-friendly method for the aminomethylation of various 3-substituted oxindoles via three-component Mannich reaction in aqueous media has been established. A variety of oxindoles containing a quaternary carbon center, which comprises an aminomethyl group were obtained smoothly in good yields (up to 93%) with this method. Particularly valuable features, such as employing cheap and readily available formalin as a useful aminomethylation Cl unit and using water as a reaction medium, are embodied in this method. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:903 / 906
页数:4
相关论文
共 47 条
  • [11] Enantioselective Organocatalytic anti-Mannich-Type Reaction of N-Unprotected 3-Substituted 2-Oxindoles with Aromatic N-Ts-aldimines
    Cheng, Liang
    Liu, Li
    Jia, Han
    Wang, Dong
    Chen, Yong-Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4650 - 4653
  • [12] The asymmetric intramolecular Heck reaction in natural product total synthesis
    Dounay, AB
    Overman, LE
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2945 - 2963
  • [13] AcOLeDMAP and BnOLeDMAP: Conformationally Restricted Nucleophilic Catalysts for Enantioselective Rearrangement of Indolyl Acetates and Carbonates
    Duffey, Trisha A.
    Shaw, Scott A.
    Vedejs, Edwin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) : 14 - +
  • [14] 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
  • [15] Asymmetric Iminium Ion Catalysis with a Novel Bifunctional Primary Amine Thiourea: Controlling Adjacent Quaternary and Tertiary Stereocenters
    Galzerano, Patrizia
    Bencivenni, Giorgio
    Pesciaioli, Fabio
    Mazzanti, Andrea
    Giannichi, Berardino
    Sambri, Letizia
    Bartoli, Giuseppe
    Melchiorre, Paolo
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (32) : 7846 - 7849
  • [16] Catalytic enantioselective fluorination of oxindoles
    Hamashima, Y
    Suzuki, T
    Takano, H
    Shimura, Y
    Sodeoka, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) : 10164 - 10165
  • [17] Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles
    Hanhan, Nadine V.
    Sahin, Aziza H.
    Chang, Toby W.
    Fettinger, James C.
    Franz, Annaliese K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) : 744 - 747
  • [18] Phosphonium Salts as Chiral Phase-Transfer Catalysts: Asymmetric Michael and Mannich Reactions of 3-Aryloxindoles
    He, Rongjun
    Ding, Changhua
    Maruoka, Keiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (25) : 4559 - 4561
  • [19] Water structure from scattering experiments and simulation
    Head-Gordon, T
    Hura, G
    [J]. CHEMICAL REVIEWS, 2002, 102 (08) : 2651 - 2669
  • [20] Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter
    Hills, ID
    Fu, GC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) : 3921 - 3924