Metal triflimide as a Lewis acid catalyst for Biginelli reactions in water

被引:96
作者
Suzuki, Ichiro [1 ]
Suzumura, Yuko [1 ]
Takeda, Kei [1 ]
机构
[1] Hiroshima Univ, Grad Sch Med Sci, Dept Synth Organ Chem, Minami Ku, Hiroshima 7358553, Japan
关键词
D O I
10.1016/j.tetlet.2006.09.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Metal triflimides such as Ni(NTf2)(2), Cu(NTf2)(2) and Yb(NTf2)(3) catalyzed the Biginelli reaction to afford 3,4-dihydropyrimidin-2(1H)-ones more efficiently in pure water at room temperature than did corresponding metal triflate salts. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7861 / 7864
页数:4
相关论文
共 42 条
[1]   Lanthanide bis(trifluoromethanesulfonyl)amides, synthesis, characterization and catalytic activity [J].
Baudry, DB ;
Dormond, A ;
Duris, F ;
Bernard, JM ;
Desmurs, JR .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 121 (02) :233-238
[2]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[3]  
Biginelli P., 1891, BER DTSCH CHEM GES, V24, P2962, DOI DOI 10.1002/CBER.189102402126
[4]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[5]   Large scale Biginelli reaction via water-based biphasic media: a green chemistry strategy [J].
Bose, AK ;
Manhas, MS ;
Pednekar, S ;
Ganguly, SN ;
Dang, H ;
He, W ;
Mandadi, A .
TETRAHEDRON LETTERS, 2005, 46 (11) :1901-1903
[6]   Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].
Bose, DS ;
Fatima, L ;
Mereyala, HB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590
[7]   Metal bis{(trifluoromethyl)sulfonyl}amide complexes: highly efficient Friedel-Crafts acylation catalysts [J].
Earle, MJ ;
Hakala, U ;
McAuley, BJ ;
Nieuwenhuyzen, M ;
Ramani, A ;
Seddon, KR .
CHEMICAL COMMUNICATIONS, 2004, (12) :1368-1369
[8]   In(OTf)3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].
Ghosh, R ;
Maiti, S ;
Chakraborty, A .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 217 (1-2) :47-50
[9]   A novel Cu-catalysed three-component one-pot synthesis of dihydro-pyrimidin-2(1H)-ones using microwaves under solvent-free conditions [J].
Gohain, M ;
Prajapati, D ;
Sandhu, JS .
SYNLETT, 2004, (02) :235-238
[10]  
HAY RW, 1987, COMPREHENSIVE COORDI, V6, P411