A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent

被引:111
作者
Xu, Jian-Ming [1 ]
Qian, Chao [1 ]
Liu, Bo-Kai [1 ]
Wu, Qi [1 ]
Lin, Xian-Fu [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
基金
中国国家自然科学基金;
关键词
ionic liquid; Michael addition; N-heterocycle; alpha; beta-unsaturated compounds;
D O I
10.1016/j.tet.2006.11.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A fast and green protocol for the Michael addition of N-heterocycles to alpha,beta-unsaturated compounds at room temperature was developed using a basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmlm]OH, as a catalyst and a reaction medium. The reactions were performed at room temperature with good yields in short reaction times (0.5-3 h). This strategy is quite general and it works with a broad range of N-heterocycles, including five-membered N-heterocycles, pyrimidines and purines. The recovered ionic liquid could be reused for several cycles with consistent activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:986 / 990
页数:5
相关论文
共 44 条
[1]   Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions [J].
Abelló, S ;
Medina, F ;
Rodríguez, X ;
Cesteros, Y ;
Salagre, P ;
Sueiras, JE ;
Tichit, D ;
Coq, B .
CHEMICAL COMMUNICATIONS, 2004, (09) :1096-1097
[2]   Multiple component reactions:: An efficient nickel-catalyzed reformatsky-type reaction and its application in the parallel synthesis of β-amino carbonyl libraries [J].
Adrian, JC ;
Snapper, ML .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2143-2150
[3]   The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids [J].
Aggarwal, A ;
Lancaster, NL ;
Sethi, AR ;
Welton, T .
GREEN CHEMISTRY, 2002, 4 (05) :517-520
[4]   Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes:: A novel, stereoselective synthesis of α,β-disubstituted β-amino carbonyl compounds via chiral auxiliary mediated azetine formation [J].
Ambhaikar, NB ;
Snyder, JP ;
Liotta, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3690-3691
[5]   Sequence specificity, reactivity, and antitumor activity of DNA-alkylating pyrrole-imidazole diamides [J].
Bando, T ;
Iida, H ;
Tao, ZF ;
Narita, A ;
Fukuda, N ;
Yamori, T ;
Sugiyama, H .
CHEMISTRY & BIOLOGY, 2003, 10 (08) :751-758
[6]   FRIEDEL CRAFTS REACTIONS IN AMBIENT-TEMPERATURE MOLTEN-SALTS [J].
BOON, JA ;
LEVISKY, JA ;
PFLUG, JL ;
WILKES, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :480-483
[7]   Process development of voriconazole: A novel broad-spectrum triazole antifungal agent [J].
Butters, M ;
Ebbs, J ;
Green, SP ;
MacRae, J ;
Morland, MC ;
Murtiashaw, CW ;
Pettman, AJ .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (01) :28-36
[8]   Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium [J].
Cai, Y ;
Wu, Q ;
Xiao, YM ;
Lv, DS ;
Lin, XF .
JOURNAL OF BIOTECHNOLOGY, 2006, 121 (03) :330-337
[9]   Alkaline protease from Bacillus subtilis catalyzed Michael addition of pyrimidine derivatives to α,β-ethylenic compounds in organic media [J].
Cai, Y ;
Sun, XF ;
Wang, N ;
Lin, XF .
SYNTHESIS-STUTTGART, 2004, (05) :671-674
[10]  
Cai Y, 2004, CHINESE CHEM LETT, V15, P594