Facile ionic liquid-mediated, three-component sequential reactions for the green, regio- and diastereoselective synthesis of furocoumarins

被引：51
|
作者：
Rajesh, Stephen Michael [1 ]
Perumal, Subbu [1 ]
Carlos Menendez, J. [2 ]
Pandian, Sokkar [1 ]
Murugesan, Ramachandran [1 ,3 ]
机构：
[1] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India
[2] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
[3] Madurai Kamaraj Univ, Sch Biol Sci, Madurai 625021, Tamil Nadu, India
来源：
TETRAHEDRON | 2012年 / 68卷 / 27-28期
关键词：
Hydroxycoumarins; Furo[3,2-c]coumarins; Ionic liquids; Domino reactions; Multicomponent reactions; MULTICOMPONENT REACTIONS; MICHAEL ADDITION; ONE-POT; MARKOVNIKOV ADDITION; DOMINO REACTIONS; N-HETEROCYCLES; CATALYST; EFFICIENT; PROTOCOL; INTERMEDIATE;
D O I：
10.1016/j.tet.2012.04.058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An environmentally friendly approach to the diastereoselective synthesis of trans-4-oxo-3-aryl-3,4-dihydro-2H-furo[3,2-c]coumarin-2-carbonitriles, trans-2-benzoy1-3-(aryl)-2H-furo[3,2-c]chromen-4(3H)-ones and trans-ethyl-4-oxo-3-(aryl)-3,4-dihydro-2H-furo[3,2-c]chromene-2-carboxylates in good yields is described. The method is based on the sequential multicomponent reactions of 4-hydroxycoumarin, aromatic aldehydes and in situ generated cyanomethylpyridinium, phenacylpyridinium/(2-ethoxy-2-oxoethyl) pyridinium ylides, in the presence of the ionic liquid [BMIm]OH, which functions both as a catalyst and the reaction medium. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5631 / 5636
页数：6
相关论文
共 50 条
  • [31] Sequential three-component reactions: synthesis, regioselectivity and application of functionalized dihydropyridines (DHPs) for the creation of fused naphthyridines
    Khan, Abu T.
    Khan, Md Musawwer
    TETRAHEDRON LETTERS, 2011, 52 (27) : 3455 - 3459
  • [32] A novel and green synthesis of indolone-N-amino acid derivatives via the Passerini three-component reactions in water
    Li, Rong-Kun
    Yang, Quan-Li
    Liu, Yi
    Li, Dong-Wei
    Huang, Nian-Yu
    Liu, Ming-Guo
    CHINESE CHEMICAL LETTERS, 2016, 27 (03) : 345 - 348
  • [33] Palladium-catalyzed three-component reaction of ferrocenyl allenes, aryl iodides and active methylene compounds: regio- and stereoselective synthesis of (E)-alkenylferrocenes
    Chen, Shufeng
    Gao, Zhenlong
    Wu, Chao
    Zhao, Haiying
    Li, Baoguo
    RSC ADVANCES, 2013, 3 (44): : 21326 - 21330
  • [34] Metal-free synthesis of cyano acrylates via cyanuric chloride-mediated three-component reactions involving a cascade consists of Knoevenagel condensation/cyano hydration/esterification
    Wan, Jie-Ping
    Jing, Yanfeng
    Liu, Yunyun
    Sheng, Shouri
    RSC ADVANCES, 2014, 4 (109) : 63997 - 64000
  • [35] A QUICK AND GREEN IONIC LIQUID-MEDIATED APPROACH FOR THE SYNTHESIS OF HIGH-PERFORMANCE, ORGANOSOLUBLE AND THERMALLY STABLE POLYIMIDES
    Mehdi Taghavi
    Mousa Ghaemy
    Marjan Hassanzadeh
    Seyed Mojtaba Amini Nasab
    Chinese Journal of Polymer Science, 2013, 31 (04) : 679 - 690
  • [36] Base-mediated isocyanide-based three-component reactions: divergent synthesis of spiro-substituted furans and pyrroles
    Wang, Hai-Ying
    Bao, Ming
    Jiang, Bo
    Li, Liang
    RSC ADVANCES, 2016, 6 (08) : 6459 - 6466
  • [37] Efficient, transition metal mediated, sequential, two- and three-component coupling reactions for the synthesis of highly substituted five-membered ring carbocycles
    Coia, Nicolas
    Bouyssi, Didier
    Balme, Genevieve
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (19) : 3158 - 3165
  • [38] A quick and green ionic liquid-mediated approach for the synthesis of high-performance, organosoluble and thermally stable polyimides
    Taghavi, Mehdi
    Ghaemy, Mousa
    Hassanzadeh, Marjan
    Mojtaba, Seyed
    Nasab, Amini
    CHINESE JOURNAL OF POLYMER SCIENCE, 2013, 31 (04) : 679 - 690
  • [39] A quick and green ionic liquid-mediated approach for the synthesis of high-performance, organosoluble and thermally stable polyimides
    Mehdi Taghavi
    Mousa Ghaemy
    Marjan Hassanzadeh
    Seyed Mojtaba Amini Nasab
    Chinese Journal of Polymer Science, 2013, 31 : 679 - 690
  • [40] Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water
    Jin, Shuai-Shuai
    Ding, Mao-Hua
    Guo, Hong-Yun
    HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 139 - 143
12345