DMAP-catalyzed four-component one-pot synthesis of highly functionalized spirooxindole-1,4-dihydropyridines derivatives in aqueous ethanol

被引:23
|
作者
Han, Chao [1 ]
Meng, Wei [1 ,2 ]
Liu, Hao [1 ]
Liu, Yanping [3 ]
Tao, Jingchao [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China
[2] Hebei United Univ, Coll Chem Engn, Tangshan 063009, Hebei, Peoples R China
[3] Zhengzhou Univ, Coll Engn Technol, Zhengzhou 450052, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
'One-pot' four-component reaction; Spirooxindole derivatives; DMAP; Tetramic acid; 1,4-Dihydropyridine; ASYMMETRIC ALDOL REACTIONS; 3-COMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; SPIROOXINDOLE DERIVATIVES; MULTICOMPONENT SYNTHESIS; BISINDOLE ALKALOIDS; ORGANIC-REACTIONS; CA2+ CHANNEL; ACID; CHEMISTRY;
D O I
10.1016/j.tet.2014.08.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, clean, and environmental friendly 'one-pot' four-component reaction was developed for assembling a novel type of spirooxindole derivatives containing dihydropyridine and pyrrolidinone. The reaction could be easily performed in aqueous ethanol with 4-DMAP as catalyst in good yields. The high efficiency and the simple and mild condition of the reaction, in addition with its avoidance of time-consuming, costly syntheses, and tedious workup, endowed the reaction with application significance. A series of spirooxindole derivatives were therefore prepared in excellent yields by using this 'one-pot' four-component reaction method. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8768 / 8774
页数:7
相关论文
共 50 条
  • [31] ONE-POT, THREE-COMPONENT SYNTHESIS OF 1,4-DIHYDROPYRIDINES IN PEG-400
    Wang, Xicun
    Gong, Haipeng
    Quan, Zhengjun
    Li, Lei
    Ye, Helin
    SYNTHETIC COMMUNICATIONS, 2011, 41 (21) : 3251 - 3258
  • [32] Rhodium(II)-Catalyzed One-Pot Four-Component Synthesis of Functionalized Polyether Macrocycles at High Concentration
    Zeghida, Walid
    Besnard, Celine
    Lacour, Jerome
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7253 - 7256
  • [33] Potassium carbonate catalyzed one pot four-component synthesis of rhodanine derivatives
    Singh, Sarangthem Joychandra
    Chauhan, S. M. S.
    TETRAHEDRON LETTERS, 2013, 54 (20) : 2484 - 2488
  • [34] One-Pot Synthesis of Highly Functionalized Bicyclic Imidazopyridinium Derivatives in Ethanol
    Chen, Liang
    Huang, Rong
    Du, Xuan-Xuan
    Yan, Sheng-Jiao
    Lin, Jun
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (02): : 1899 - 1905
  • [35] One-pot, three-component synthesis of highly substituted pyridines and 1,4-dihydropyridines by using nanocrystalline magnesium oxide
    M. Lakshmi Kantam
    Koosam Mahendar
    Suresh Bhargava
    Journal of Chemical Sciences, 2010, 122 : 63 - 69
  • [36] One-pot, three-component synthesis of highly substituted pyridines and 1,4-dihydropyridines by using nanocrystalline magnesium oxide
    Kantam, M. Lakshmi
    Mahendar, Koosam
    Bhargava, Suresh
    JOURNAL OF CHEMICAL SCIENCES, 2010, 122 (01): : 63 - 69
  • [37] Efficient One-Pot Synthesis of Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-Diazaheterocycle Fragments via Four-Component Reaction
    Alizadeh, Abdolali
    Firuzyar, Tahereh
    Mikaeili, Azadeh
    SYNTHESIS-STUTTGART, 2010, (22): : 3913 - 3917
  • [38] Solvent-free one-pot synthesis of highly functionalized benzothiazolediamides via Ugi four-component reaction
    Sheikholeslami-Farahani, F.
    Shahvelayati, A. S.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2015, 47 (03): : 830 - 836
  • [39] One-pot synthesis of functionalized piperid-4-ones: A four-component condensation
    Clarke, Paul A.
    Zaytsev, Andrey V.
    Morgan, Tyson W.
    Whitwood, Adrian C.
    Wilson, Claire
    ORGANIC LETTERS, 2008, 10 (13) : 2877 - 2880
  • [40] Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by L-Proline in Aqueous Medium
    Li, Yuling
    Chen, Hui
    Shi, Chunling
    Shi, Daqing
    Ji, Shunjun
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (02): : 231 - 237