One-pot synthesis of β-amido ketones using Bronsted acidic ionic liquid as an efficient and reusable catalyst

被引：18

作者：

Deshmukh, Krishna M. ^{[1
]}

Qureshi, Ziyauddin S. ^{[1
]}

Nandurkar, Nitin S. ^{[1
]}

Bhanage, Bhalchandra M. ^{[1
]}

机构：

[1] Univ Bombay, Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2009年 / 87卷 / 02期

关键词：

ionic liquids; multicomponent reactions; beta-amido ketones; one-pot synthesis; DAKIN-WEST REACTION; SILICA SULFURIC-ACID; ACETAMIDO KETONES; MULTICOMPONENT SYNTHESIS; CARBONYL-COMPOUNDS; MANNICH REACTION; SOLVENT; LIBRARIES; CHLORIDE;

D O I：

10.1139/V08-173

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient protocol was developed for one-pot condensation of an aldehyde, ketone, acetyl chloride, and nitriles catalyzed by a stable and reusable 1-methyl-imidazolium hydrogen sulfate ([Hmim][HSO4]) as a Bronsted acidic ionic liquid. The system tolerated a variety of functional groups affording the corresponding beta-amido ketones in moderate to good yields under milder operating conditions.

引用

页码：401 / 405

页数：5

共 25 条

[1] Efficient combination of recyclable task specific ionic liquid and microwave dielectric heating for the synthesis of lipophilic esters [J].

Arfan, A ;

Bazureau, JP .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (06) :743-748

[2] Montmorillonite K10 clay:: An efficient catalyst for the one-pot stereoselective synthesis of β-acetanxido ketones [J].

Bahulayan, D ;

Das, SK ;

Iqbal, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5735-5738

[3]

CASIMIR JR, 1995, TETRAHEDRON LETT, V36, P4797

[4] [Hmim][NO3] -: an efficient solvent and promoter in the oxidative aromatic chlorination [J].

Chiappe, Cinzia ;

Leandri, Elsa ;

Tebano, Marianna .

GREEN CHEMISTRY, 2006, 8 (08) :742-745

[5] Reactivity of ionic liquids [J].

Chowdhury, Shahana ;

Mohan, Ram S. ;

Scott, Janet L. .

TETRAHEDRON, 2007, 63 (11) :2363-2389

[6] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].

Cole, AC ;

Jensen, JL ;

Ntai, I ;

Tran, KLT ;

Weaver, KJ ;

Forbes, DC ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963

[7] METABOLIC PRODUCTS OF MICROORGANISMS .154. NIKKOMYCIN, A NEW INHIBITOR OF FUNGAL CHITIN SYNTHESIS [J].

DAHN, U ;

HAGENMAIER, H ;

HOHNE, H ;

KONIG, WA ;

WOLF, G ;

ZAHNER, H .

ARCHIVES OF MICROBIOLOGY, 1976, 107 (02) :143-160

[8]

Dakin HD, 1928, J BIOL CHEM, V78, P745

[9] ZrOCl2•8H2O:: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones [J].

Ghosh, R ;

Maiti, S ;

Chakraborty, A ;

Chakraborty, S ;

Mukherjee, AK .

TETRAHEDRON, 2006, 62 (17) :4059-4064

[10] One-pot multicomponent synthesis of p-acetamido ketones based on BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride [J].

Ghosh, R ;

Maiti, S ;

Chakraborty, A .

SYNLETT, 2005, (01) :115-118

← 1 2 3 →