A Highly Efficient Michael Addition of Indoles to α,β-Unsaturated Electron-Deficient Compounds in Acidic SDS Micellar Media

被引：19

作者：

Jafari, A. A. ^{[1
]}

Moradgholi, F. ^{[1
]}

Tamaddon, F. ^{[1
]}

机构：

[1] Yazd Univ, Fac Sci, Dept Chem, Yazd 89195741, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2009年 / 6卷 / 03期

关键词：

Michael addition; Indole; alpha; beta-Unsaturated electron-deficient compounds; Micellar media; CATALYZED CONJUGATE ADDITION; SURFACTANT-COMBINED CATALYST; ASYMMETRIC HYDROGENATION; ORGANIC-REACTIONS; IONIC LIQUID; WATER; KETONES; OLEFINS; ALPHA; PYRROLE;

D O I：

10.1007/BF03246538

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Michael addition of indoles to alpha,beta-unsaturated electron deficient compounds was catalyzed efficiently at room temperature in acidic micellar solution of sodium dodecyl sulfate (SDS). The substitution on the indole nucleus occurred exclusively at the 3-position in good to excellent yields, and no N-alkylation products were observed.

引用

页码：588 / 593

页数：6

共 41 条

[1] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].

Alam, MM ;

Varala, R ;

Adapa, SR .

TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119

[2] 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

[3]

Anastas P., 1998, GREEN CHEM THEORY PR

[4] 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

[5] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].

Bandini, M ;

Cozzi, PG ;

Giacomini, M ;

Melchiorre, P ;

Selva, S ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704

[6] The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].

Bartoli, G ;

Bartolacci, M ;

Bosco, M ;

Foglia, G ;

Giuliani, A ;

Marcantoni, E ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597

[7]

Berezin I.V., 1973, Russian Chemical Reviews, V42, P787, DOI [DOI 10.1070/RC1973V042N10ABEH002744, 10.1070/RC1973v042n10ABEH002744, 10.1070/rc1973v042n10abeh002744]

[8] EXCITING RESULTS FROM THE FIELD OF HOMOGENEOUS 2-PHASE CATALYSIS [J].

CORNILS, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1575-1577

[9]

Cramer C.J., 1994, STRUCTURE REACTIVITY

[10]

Dwars T, 1998, ANGEW CHEM INT EDIT, V37, P2851, DOI 10.1002/(SICI)1521-3773(19981102)37:20<2851::AID-ANIE2851>3.0.CO

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