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 50 条
  • [1] Direct-type catalytic three-component Mannich reaction in aqueous media
    Ollevier, Thierry
    Nadeau, Etienne
    Guay-Begin, Andree-Anne
    TETRAHEDRON LETTERS, 2006, 47 (47) : 8351 - 8354
  • [2] Microwave-Assisted Synthesis of 3-Substituted Indole Derivatives via Three-Component Domino Reaction
    Lin, Wei
    Hu, Xiuxiu
    Wang, Yazhen
    Song, Shuai
    Zhang, Mengye
    Shi, Daqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (04) : 855 - 862
  • [3] One-pot three-component reaction: Synthesis of substituted β-cyanocarbonyls in aqueous media
    Soleimani, Ebrahim
    Khodaei, Mohammad Mehdi
    Koshvandi, Afsaneh Taheri Kal
    COMPTES RENDUS CHIMIE, 2012, 15 (04) : 273 - 277
  • [4] Zn-Mediated Synthesis of 3-Substituted Indoles Using a Three-Component Reaction Approach
    Anselmo, Daniele
    Escudero-Adan, Eduardo C.
    Martinez Belmonte, Marta
    Kleij, Arjan W.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (29) : 4694 - 4700
  • [5] A Facile and Clean Synthesis of Pyrimidine Derivatives via Three-component Reaction in Aqueous Media
    Shi Daqing
    Shi Jingwen
    Rong Shaofeng
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (05) : 791 - 796
  • [6] One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)
    Zareyee, Daryoush
    Alizadeh, Hamidreza
    RSC ADVANCES, 2014, 4 (71): : 37941 - 37946
  • [7] Efficient synthesis of 3-substituted indoles via a base-free copper-catalysed three-component reaction in water
    Jiang, Haojie
    Wang, Leilei
    Xie, Jianwei
    JOURNAL OF CHEMICAL RESEARCH, 2016, (06) : 338 - 340
  • [8] A highly efficient and eco-friendly method for the synthesis of 1,3-indandione ring-fused 3-oxindoles bearing two contiguous quaternary stereocenters via an aldol reaction in aqueous media
    Liu, Xiong-Li
    Pan, Bo-Wen
    Zhang, Wen-Hui
    Yang, Chao
    Yang, Jun
    Shi, Yang
    Feng, Ting-Ting
    Zhou, Ying
    Yuan, Wei-Cheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (02) : 601 - 611
  • [9] Facile Access to Amido (Thio)xanthates under Eco-Friendly Conditions by One-Pot Three-Component Reaction (3-CR)
    Franz, Max
    Stalling, Timo
    Schaper, Raoul
    Schmidtmann, Marc
    Martens, Juergen
    SYNTHESIS-STUTTGART, 2017, 49 (17): : 4045 - 4054
  • [10] SIMPLE AND EFFICIENT METHOD FOR THREE-COMPONENT SYNTHESIS OF SPIROOXINDOLES IN AQUEOUS AND SOLVENT-FREE MEDIA
    Mobinikhaledi, Akbar
    Foroughifar, Naser
    Fard, Mohammad Ali Bodaghi
    SYNTHETIC COMMUNICATIONS, 2011, 41 (03) : 441 - 450
12345