Poly(N-vinylimidazole) as an efficient and recyclable catalyst of the aza-Michael reaction in water

被引：22

作者：

Beletskaya, I. P. ^{[1
]}

Tarasenko, E. A. ^{[1
]}

Khokhlov, A. R. ^{[2
]}

Tyurin, V. S. ^{[1
]}

机构：

[1] Russian Acad Sci, Frumkin Inst Phys Chem & Electrochem, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Fac Chem, Moscow 119992, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 46卷 / 04期

关键词：

BASIC IONIC LIQUID; CONJUGATE ADDITION; ALPHA; BETA-ETHYLENIC COMPOUNDS; ALIPHATIC-AMINES; AROMATIC-AMINES; N-HETEROCYCLES; ACID; BETA; GREEN; SYSTEM;

D O I：

10.1134/S1070428010040019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Poly(N-vinylimidazole) effectively catalyzed Michael addition of 1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, uracil, oxazolidin-2-one, and succinimide to but-3-en-2-one, cyclohex-2-en-1-one, methyl acrylate, and methyl vinyl sulfone in water at room temperature. The catalyst can readily be regenerated and repeatedly used at least five times without loss in activity, as shown in the reaction of 1H-1,2,4-triazole with but-3-en-2-one as an example.

引用

页码：461 / 467

页数：7

共 69 条

[1] Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions [J].

Alleti, Ramesh ;

Oh, Woon Su ;

Perambuduru, Meher ;

Ramana, C. V. ;

Reddy, V. Prakash .

TETRAHEDRON LETTERS, 2008, 49 (21) :3466-3470

[2] Efficient Bronsted acid-catalyzed aza-Michael reaction of amides and ureas with α,β-unsaturated enones under high-pressure conditions [J].

Azad, Saleha ;

Kobayashi, Tomohiro ;

Nakano, Keiji ;

Ichikawa, Yoshiyasu ;

Kotsuki, Hiyoshizo .

TETRAHEDRON LETTERS, 2009, 50 (01) :48-50

[3] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

[4] Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions [J].

Bartoli, G ;

Bartolacci, M ;

Giuliani, A ;

Marcantoni, E ;

Massaccesi, M ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :169-174

[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] Poly(N-vinylimidazole) as efficient and recyclable catalyst for the addition of thiols to michael acceptors in aqueous medium [J].

Beletskaya, I. P. ;

Tarasenko, E. A. ;

Khokhlov, A. R. ;

Tyurin, V. S. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (11) :1733-1736

[7] Palladium supported on poly(N-vinylimidazole) or poly(N-vinylimidazole-co-N-vinylcaprolactam) as a new recyclable catalyst for the Mizoroki-Heck reaction [J].

Beletskaya, Irina P. ;

Khokhlov, Alexey R. ;

Tarasenko, Elena A. ;

Tyurin, Vladimir S. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (20) :4402-4406

[8]

Bender M. L., 1984, BIOORGANIC CHEM ENZY

[9]

BEREZIN IV, 1977, OSNOVY FIZICHESKOI K, P280

[10]

BERKESSEL A, 2005, BIOMIMETIC CONCEPTS

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