Carbohydrate-based tolylsulfonyl hydrazines: Effective catalysts for Michael addition of indoles to electron-deficient olefins in water

被引:32
作者
Wu, Peng [1 ,2 ]
Wan, Yiqian [2 ]
Cai, Jiwen [1 ,2 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510275, Guangdong, Peoples R China
[2] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
关键词
carbohydrate-based tolylsulfonyl hydrazines; catalyst; Michael addition of indole; water;
D O I
10.1055/s-2008-1072735
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbohydrate-based tolylsulfonyl hydrazines were used for the first time to catalyze the Michael reaction of indoles to electron-deficient olefins in aqueous media to afford 3-substituted indole derivatives in good to excellent yields at room temperature.
引用
收藏
页码:1193 / 1198
页数:6
相关论文
共 32 条
[1]   Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition [J].
An, Li-Tao ;
Zou, Jian-Ping ;
Zhang, Li-Li ;
Zhang, Yong .
TETRAHEDRON LETTERS, 2007, 48 (24) :4297-4300
[2]   Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water [J].
Azizi, Najmedin ;
Arynasab, Fezzeh ;
Saidi, Mohammad R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4275-4277
[3]   Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors:: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate [J].
Bartoli, G ;
Bosco, M ;
Giuli, S ;
Giuliani, A ;
Lucarelli, L ;
Marcantoni, E ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1941-1944
[4]   Direct organocatalytic aldol reactions in buffered aqueous media [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025
[5]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[6]   Regio- and diastereoselective three-component syntheses of homoallylic amines in aqueous media catalyzed by Bronsted acids [J].
Deng, Dong-Sheng ;
Liu, Ping ;
Cai, Jiwen .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) :1594-1598
[7]   Stereoselective aldol reactions catalyzed by acyclic amino acids in aqueous micelles [J].
Deng, Dong-Sheng ;
Cai, Jiwen .
HELVETICA CHIMICA ACTA, 2007, 90 (01) :114-120
[8]   Aqueous aldol catalysis by a nicotine metabolite [J].
Dickerson, TJ ;
Janda, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3220-3221
[9]   The facile and efficient Michael addition of indoles and pyrrole to α, β-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3]3H2O in water [J].
Firouzabadi, H ;
Iranpoor, N ;
Nowrouzi, F .
CHEMICAL COMMUNICATIONS, 2005, (06) :789-791
[10]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075