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
  • [1] A simple, green and one-pot four-component synthesis of 1,4-dihydropyridines and their aromatization
    Das Sharma, Saikat
    Hazarika, Parasa
    Konwar, Dilip
    CATALYSIS COMMUNICATIONS, 2008, 9 (05) : 709 - 714
  • [2] Synthesis of Functionalized 1-Benzamido-1,4-dihydropyridines via a One-Pot Two-Step Four-Component Reaction
    Sun, Jing
    Shen, Guoliang
    Xie, Yajing
    Yan, Chaoguo
    CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (11) : 1143 - 1150
  • [3] One-Pot, Pseudo Five-Component Synthesis of Spirooxindole Derivatives Containing Fused 1,4-Dihydropyridines in Water
    Alizadeh, Abdolali
    Mikaeili, Azadeh
    Firuzyar, Tahereh
    SYNTHESIS-STUTTGART, 2012, 44 (09): : 1380 - 1384
  • [4] A one-pot four-component reaction providing quinoline-based 1,4-dihydropyridines
    Ghandi, Mehdi
    Zarezadeh, Nahid
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (08) : 1313 - 1324
  • [5] A one-pot four-component reaction providing quinoline-based 1,4-dihydropyridines
    Mehdi Ghandi
    Nahid Zarezadeh
    Journal of the Iranian Chemical Society, 2015, 12 : 1313 - 1324
  • [6] Synergistic Catalysis of Ag(I) and Organo-N-heterocyclic Carbenes: One-Pot Synthesis of New Anticancer Spirooxindole-1,4-dihydropyridines
    Balaboina, Ramesh
    Thirukovela, Narasimha Swamy
    Kankala, Shravankumar
    Balasubramanian, Sridhar
    Bathula, Surendar Reddy
    Vadde, Ravinder
    Jonnalagadda, Sreekantha B.
    Vasam, Chandra Sekhar
    CHEMISTRYSELECT, 2019, 4 (09): : 2562 - 2567
  • [7] Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst
    Maleki A.
    Kamalzare M.
    Aghaei M.
    Journal of Nanostructure in Chemistry, 2015, 5 (1) : 95 - 105
  • [8] An expedient synthesis strategy to the 1,4-dihydropyridines and pyrido[1,2-a]quinoxalines: iodine catalyzed one-pot four-component domino reactions
    Rezvanian, Atieh
    TETRAHEDRON, 2016, 72 (41) : 6428 - 6435
  • [9] An efficient copper catalyzed one-pot, four-component, and diastereoselective synthesis of highly functionalized ferrocenyl azetidinimines
    Gouthaman, Siddan
    Shanmugam, Ponnusamy
    Mandal, Asit Baran
    TETRAHEDRON LETTERS, 2013, 54 (23) : 3007 - 3010
  • [10] A one-pot, four-component synthesis of α-carboline derivatives
    Ghahremanzadeh, Ramin
    Ahadi, Somayeh
    Bazgir, Ayoob
    TETRAHEDRON LETTERS, 2009, 50 (52) : 7379 - 7381