Convenient and efficient protocols for coumarin synthesis via Pechmann condensation in neutral ionic liquids

被引：52

作者：

Potdar, MK ^{[1
]}

Rasalkar, MS ^{[1
]}

Mohile, SS ^{[1
]}

Salunkhe, MM ^{[1
]}

机构：

[1] Inst Sci, Dept Chem, Bombay 400032, Maharashtra, India

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2005年 / 235卷 / 1-2期

关键词：

coumarin synthesk; Pechmann condensation; 1-butyl-3-methylimidazolium hexafluorophosphate;

D O I：

10.1016/j.molcata.2005.04.007

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：

Neutral ionic liquids with catalytic amount of acid have been employed for coumarin synthesis via Pechmann condensation of phenols and ethyl acetoacetate under ambient conditions. The reaction was also successfully carried out at high temperature in 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, without the use of any acid catalyst. The possibility of Bronsted acidic ionic liquids catalysing this reaction has also been investigated. Ionic liquids were recycled efficiently. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：249 / 252

页数：4

共 28 条

[1]

CHAUDHARI DD, 1983, CHEM IND-LONDON, P568

[2]

de la Hoz A, 1999, SYNLETT, P608

[3] Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction [J].

Dere, RT ;

Pal, RR ;

Patil, PS ;

Salunkhe, MM .

TETRAHEDRON LETTERS, 2003, 44 (28) :5351-5353

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

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

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

[5] Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10:: application to the preparation of 4-substituted 7-aminocoumarins [J].

Frère, S ;

Thiéry, V ;

Besson, T .

TETRAHEDRON LETTERS, 2001, 42 (15) :2791-2794

[6] Fries rearrangement in ionic melts [J].

Harjani, JR ;

Nara, SJ ;

Salunkhe, MM .

TETRAHEDRON LETTERS, 2001, 42 (10) :1979-1981

[7] SYNTHESIS OF 7-HYDROXYCOUMARINS CATALYZED BY SOLID ACID CATALYSTS [J].

HOEFNAGEL, AJ ;

GUNNEWEGH, EA ;

DOWNING, RS ;

VANBEKKUM, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :225-226

[8] USE OF CATION EXCHANGE RESINS IN ORGANIC REACTIONS .1. VON PECHMANN REACTION [J].

JOHN, EV ;

ISRAELSTAM, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (01) :240-&

[9] The first Bischler-Napieralski cyclization in a room temperature ionic liquid [J].

Judeh, ZMA ;

Ching, CB ;

Bu, J ;

McCluskey, A .

TETRAHEDRON LETTERS, 2002, 43 (29) :5089-5091

[10] L-proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric aldol reactions [J].

Loh, TP ;

Feng, LC ;

Yang, HY ;

Yang, JY .

TETRAHEDRON LETTERS, 2002, 43 (48) :8741-8743

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