A fast, highly efficient and green protocol for Michael addition of active methylene compounds to styrylisoxazoles using task-specific basic ionic liquid [bmIm]OH as catalyst and green solvent

被引：0

作者：

Rajanarendar, E. ^{[1
]}

Murthy, K. Rama ^{[1
]}

Shaik, Firoz Pasha ^{[1
]}

Reddy, M. Nagi ^{[1
]}

机构：

[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India

来源：

INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2011年 / 50卷 / 04期

关键词：

Active methylene compounds; styrylisoxazole; nitroisoxazole; Michael addition; task-specific basic ionic liquid [bmIm]OH; MICROWAVE-ASSISTED PREPARATION; 1,3-DICARBONYL COMPOUNDS; HETEROCYCLES;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fast, highly efficient and green protocol for the Michael addition of active methylene compounds to styrylisoxazoles at room temperature has been investigated using task-specific basic ionic liquid, 3-butyl-I-methyl imidazolium hydroxide, [bmIm]OH, as a catalyst and green reaction medium. The reactions proceeded with excellent yields in short reaction times. The strategy is quite general and works with a variety of active methylene compounds. The ionic liquid can be recycled for subsequent reactions with consistent activity.

引用

页码：587 / 592

页数：6

共 34 条

[1] The reactivity of 3-methyl-4-nitro-5-styrylisoxazole with some bis-enolisable ketones [J].

Adamo, MFA ;

Chimichi, S ;

De Sio, F ;

Donati, D ;

Sarti-Fantoni, P .

TETRAHEDRON LETTERS, 2002, 43 (23) :4157-4160

[2] Mannich-type reaction promoted by an ionic liquid [J].

Akiyama, T ;

Suzuki, A ;

Fuchibe, K .

SYNLETT, 2005, (06) :1024-1026

[3]

Bergman E., 1959, ORG REACT, V10, P179, DOI DOI 10.1002/0471264180.OR010.03

[4] 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

[5] 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

[6]

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

[7] Catalysis and regioselectivity in the Michael addition of azoles, kinetic vs thermodynamic control [J].

Horvath, A .

TETRAHEDRON LETTERS, 1996, 37 (25) :4423-4426

[8]

JUNG ME, 1991, COMPREHENSIVE ORGANI, P4

[9] Microwave-assisted preparation of 1-butyl-3-methylimidazolium tetrachlorogallate and its catalytic use in acetal formation under mild conditions [J].

Kim, YJ ;

Varma, RS .

TETRAHEDRON LETTERS, 2005, 46 (43) :7447-7449

[10]

KOBAYASHI S, 1994, SYNLETT, P689

← 1 2 3 4 →