Task-Specific Ionic Liquid as Reagent and Reaction Medium for the One-Pot Horner-Wadsworth-Emmons-Type Reaction Under Microwave Irradiation

被引：25

作者：

Valizadeh, Hassan ^{[1
]}

Shockravi, Abbas ^{[2
]}

机构：

[1] Azarbaijan Univ Tarbiat Moallem, Dept Chem, Fac Sci, Tabriz, Iran

[2] Univ Tarbiat Moallem, Fac Chem, Tehran, Iran

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 24期

关键词：

Coumarin; Horner-Wadsworth-Emmons reaction; microwave; task-specific ionic liquid; SOLVENT-FREE CONDITIONS; WITTIG REACTIONS; COUMARIN DERIVATIVES; ROOM-TEMPERATURE; AROMATIC-COMPOUNDS; CATALYTIC-SYSTEMS; REUSABLE CATALYST; EFFICIENT; IL-OPPH2; ALCOHOLS;

D O I：

10.1080/00397910902898650

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A task-specific imidazolium-based phosphinite ionic liquid (IL-OPPh2) was used as the dual solvent-reagent for the synthesis of E-cinamates and coumarin derivatives via the one-pot Horner-Wadsworth-Emmons-type reaction. The ionic liquid containing its corresponding phosphinite moiety was reacted with a-chloro esters and benzaldehyde or salicylaldehyde derivatives in the presence of sodium methoxide under microwave irradiation to produce the related E-cinamates or coumarins, respectively. The satisfactory results were obtained with good yields, short reaction time, and simple experimental procedure.

引用

页码：4341 / 4349

页数：9

共 37 条

[1]

[Anonymous], 1992, The Production and Application of Fluorescent Brightening Agents

[2]

[Anonymous], 1992, APPL ORGANOMET CHEM

[3] Ionic liquids and chirality: opportunities and challenges [J].

Baudequin, C ;

Baudoux, J ;

Levillain, J ;

Cahard, D ;

Gaumont, AC ;

Plaquevent, JC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093

[4] Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].

Bigi, F ;

Chesini, L ;

Maggi, R ;

Sartori, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035

[5] A highly selective arene hydrogenation catalyst that operates in ionic liquid [J].

Boxwell, CJ ;

Dyson, PJ ;

Ellis, DJ ;

Welton, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9334-9335

[6] An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition [J].

Cravotto, G ;

Nano, GM ;

Palmisano, G ;

Tagliapietra, S .

TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :707-709

[7] Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl) methanes, and N-alkyl and N-arylimides in ionic liquids [J].

Dabiri, M. ;

Salehi, P. ;

Baghbanzadeh, M. ;

Shakouri, M. ;

Otokesh, S. ;

Ekrami, T. ;

Doosti, R. .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2007, 4 (04) :393-401

[8] DALBERGIA SPECIES .6. OCCURRENCE OF MELANNEIN IN GENUS DALBERGIA [J].

DONNELLY, BJ ;

DONNELLY, DM ;

OSULLIVAN, AM .

TETRAHEDRON, 1968, 24 (06) :2617-+

[9] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[10] Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions [J].

Earle, MJ ;

Katdare, SP ;

Seddon, KR .

ORGANIC LETTERS, 2004, 6 (05) :707-710

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