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
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 08期
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
  • [1] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
  • [2] 2-E
  • [3] Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles
    Bella, M
    Kobbelgaard, S
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3670 - 3671
  • [4] Dimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives
    Bui, Tommy
    Candeias, Nuno R.
    Barbas, Carlos F., III
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) : 5574 - +
  • [5] Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine
    Bui, Tommy
    Syed, Salahuddin
    Barbas, Carlos F., III
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) : 8758 - +
  • [6] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
    Chen, Wen-Bing
    Wu, Zhi-Jun
    Pei, Qing-Lan
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3132 - 3135
  • [7] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine
    Chen, Wen-Bing
    Du, Xi-Lin
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. TETRAHEDRON, 2010, 66 (07) : 1441 - 1446
  • [8] Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive
    Chen, Wen-Bing
    Liao, Yu-Hua
    Du, Xi-Lin
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. GREEN CHEMISTRY, 2009, 11 (09) : 1465 - 1476
  • [9] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
    Chen, Xiao-Hua
    Wei, Qiang
    Luo, Shi-Wei
    Xiao, Han
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13819 - 13825
  • [10] Highly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles
    Cheng, Liang
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    [J]. ORGANIC LETTERS, 2009, 11 (17) : 3874 - 3877
12345