Beckmann rearrangement of oximes catalyzed by cyanuric chloride in ionic liquids

被引：26

作者：

Betti, Cecilia ^{[1
]}

Landini, Dario ^{[1
]}

Maia, Angelamaria ^{[2
]}

Pasia, Maurizio ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] ISTM, Ist CNR, I-20133 Milan, Italy

来源：

SYNLETT | 2008年 / 06期

关键词：

oximes; amides; Beckmann rearrangement; ionic liquids; cyanuric chloride catalysis;

D O I：

10.1055/s-2008-1042804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Beckmann rearrangement of a variety of ketoximes has been carried out in imidazolium-based ionic liquids in the presence of catalytic amounts of 2,4,6-trichloro[1,3,5]triazine. This mild and 'green' procedure is highly regioselective affording the corresponding N-substituted amides in very good to quantitative yields. The ionic liquids were easily recovered and recycled several times.

引用

页码：908 / 910

页数：3

共 19 条

[1] Reactivity of anionic nucleophiles in ionic liquids and molecular solvents [J].

Betti, Cecilia ;

Landini, Dario ;

Maia, Angelamaria .

TETRAHEDRON, 2008, 64 (08) :1689-1695

[2] 'Metal ion electrophilic catalysis' in ring-opening reactions of 1,2-epoxides by metal halides in ionic liquids [J].

Betti, Cecilia ;

Landini, Dario ;

Maia, Angelamaria .

SYNLETT, 2006, (09) :1335-1338

[3] Reactivity of ionic liquids [J].

Chowdhury, Shahana ;

Mohan, Ram S. ;

Scott, Janet L. .

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

[4] Beckmann rearrangement of oximes under very mild conditions [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6272-6274

[5] Characterizing ionic liquids as reaction media through a chemical probe [J].

Dichiarante, Valentina ;

Betti, Cecilia ;

Fagnoni, Maurizio ;

Maia, Angelamaria ;

Landini, Dario ;

Albini, Angelo .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (06) :1834-1841

[6] Cyanuric chloride as a mild and active Beckmann rearrangement catalyst [J].

Furuya, Y ;

Ishihara, K ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11240-11241

[7]

Gawley R. E., 1988, ORG REACTIONS, P1, DOI [10.1002/0471264180.or035.01, DOI 10.1002/0471264180.OR035.01]

[8] A novel task-specific ionic liquid for Beckmann rearrangement: a simple and effective way for product separation [J].

Gui, JZ ;

Deng, YQ ;

Hu, ZD ;

Sun, ZL .

TETRAHEDRON LETTERS, 2004, 45 (12) :2681-2683

[9] Clean Beckmann rearrangement of cyclohexanone oxime in caprolactam-based Bronsted acidic ionic liquids [J].

Guo, S ;

Du, ZY ;

Zhang, SG ;

Li, DM ;

Li, ZP ;

Deng, YQ .

GREEN CHEMISTRY, 2006, 8 (03) :296-300

[10] Anion nucleophilicity in ionic liquids: a comparison with traditional molecular solvents of different polarity [J].

Landini, D ;

Maia, A .

TETRAHEDRON LETTERS, 2005, 46 (23) :3961-3963

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