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
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