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
  • [21] Graphite oxide catalyzed one-pot synthesis of highly functionalized spirodibenzo[1,4]diazepine derivatives in aqueous ethanol medium
    Sarkar, Rajib
    Dam, Binoyargha
    Kyndiah, Lenida
    Sarkar, Fillip Kumar
    Gajurel, Sushmita
    Pal, Amarta Kumar
    GREEN CHEMISTRY, 2022, 24 (14) : 5579 - 5591
  • [22] Microwave-Assisted One-Step Four-Component Reaction for Synthesis of 1,4-Dihydropyridines Catalyzed by Triethylamine
    Khumalo, Mandlenkosi Robert
    Maddila, Surya Narayana
    Maddila, Suresh
    Jonnalagadda, Sreekantha B.
    CHEMISTRYSELECT, 2019, 4 (43): : 12503 - 12506
  • [23] DBU-Catalyzed Three-Component One-Pot Synthesis of Highly Functionalized Pyridines in Aqueous Ethanol
    Mamgain, Ritu
    Singh, Rain
    Rawat, Diwan S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (01) : 69 - 73
  • [24] A straightforward and sustainable one-pot, four-component synthesis of rhodanine derivatives
    Azizi, Najmedin
    Hasani, Morteza
    Khajeh, Meysam
    Edrisi, Mahtab
    TETRAHEDRON LETTERS, 2015, 56 (10) : 1189 - 1192
  • [25] Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives
    Guo, Rui-Yun
    An, Zhi-Min
    Mo, Li-Ping
    Yang, Shu-Tao
    Liu, Hong-Xia
    Wang, Shu-Xia
    Zhang, Zhan-Hui
    TETRAHEDRON, 2013, 69 (47) : 9931 - 9938
  • [26] One-pot, four-component synthesis of spiroindoloquinazoline derivatives as phospholipase inhibitors
    Beyrati, Maryam
    Forutan, Maryam
    Hasaninejad, Alireza
    Rakovsky, Erik
    Babaei, Somayyeh
    Maryamabadi, Ammar
    Mohebbi, Gholamhossein
    TETRAHEDRON, 2017, 73 (34) : 5144 - 5152
  • [27] One-pot four-component synthesis of highly substituted pyrroles in gluconic acid aqueous solution
    Li, Bao-Le
    Li, Pei-He
    Fang, Xue-Na
    Li, Chun-Xiao
    Sun, Jing-Lei
    Mo, Li-Ping
    Zhang, Zhan-Hui
    TETRAHEDRON, 2013, 69 (34) : 7011 - 7018
  • [28] One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction
    Debache, Abdelimadjid
    Boulcina, Raouf
    Belfaitah, Ali
    Rhouati, Salah
    Carboni, Bertrand
    SYNLETT, 2008, (04) : 509 - 512
  • [29] DPTA-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines
    Li, Jianjun
    He, Ping
    Yu, Chuanming
    TETRAHEDRON, 2012, 68 (22) : 4138 - 4144
  • [30] Silica-supported Perchloric Acid Catalyzed One-pot Synthesis of 1,4-Dihydropyridines
    Ramesh, Dasari
    Rajaram, Singanaboina
    Narasimhulu, Manchala
    Reddy, Thummalpally Srikanth
    Mahesh, Kondempudi Chinni
    Manasa, Gajji
    Venkateswarlu, Yenamandra
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2471 - 2475