ZrOCl2•8H2O as a highly efficient and the moisture tolerant Lewis acid catalyst for Michael addition of amines and indoles to α,β-unsaturated ketones under solvent-free conditions

被引：76

作者：

Firouzabadi, H ^{[1
]}

Iranpoor, N ^{[1
]}

Jafarpour, M ^{[1
]}

Ghaderi, A ^{[1
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2006年 / 252卷 / 1-2期

关键词：

ZrOCl2 center dot 8H(2)O; Michael reaction; amine; indole; alpha; beta-unsaturated ketones; solvent-free;

D O I：

10.1016/j.molcata.2005.11.025

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The 1,4-conjugate addition of indoles and amines to cyclic and acyclic a, D-unsaturated ketones for C-N bond formation was efficiently carried out under solvent-free conditions at 50 degrees C using a catalytic amount of ZrOCl2-8H(2)O as a moisture tolerant Lewis acid. The reusability of the catalyst has been successfully examined without noticeable loss of its catalytic activity. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：150 / 155

页数：6

共 52 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]

[Anonymous], CHEM AMINO GROUP

[3] THE ADDITION OF SECONDARY AMINES TO SOME ALPHA-BENZAL KETONES [J].

BALTZLY, R ;

LORZ, E ;

RUSSELL, PB ;

SMITH, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (03) :624-628

[4] 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

[5] Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].

Bartoli, G ;

Bosco, M ;

Marcantoni, E ;

Petrini, M ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055

[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] CATALYSIS OF THE SPECIFIC MICHAEL ADDITION - THE EXAMPLE OF ACRYLATE ACCEPTORS [J].

CABRAL, J ;

LASZLO, P ;

MAHE, L ;

MONTAUFIER, MT ;

RANDRIAMAHEFA, SL .

TETRAHEDRON LETTERS, 1989, 30 (30) :3969-3972

[8]

CARDILLO G, 1996, CHEM SOC REV, P117

[9]

Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259

[10] Rapid, highly efficient and stereoselective deoxygenation of epoxides by ZrCl4/NaI [J].

Firouzabadi, H ;

Iranpoor, N ;

Jafarpour, M .

TETRAHEDRON LETTERS, 2005, 46 (23) :4107-4110

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