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
收藏
页码：908 / 910
页数：3
相关论文
共 19 条
  • [1] Reactivity of anionic nucleophiles in ionic liquids and molecular solvents
    Betti, Cecilia
    Landini, Dario
    Maia, Angelamaria
    [J]. 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
    Betti, Cecilia
    Landini, Dario
    Maia, Angelamaria
    [J]. SYNLETT, 2006, (09) : 1335 - 1338
  • [3] Reactivity of ionic liquids
    Chowdhury, Shahana
    Mohan, Ram S.
    Scott, Janet L.
    [J]. TETRAHEDRON, 2007, 63 (11) : 2363 - 2389
  • [4] Beckmann rearrangement of oximes under very mild conditions
    De Luca, L
    Giacomelli, G
    Porcheddu, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) : 6272 - 6274
  • [5] Characterizing ionic liquids as reaction media through a chemical probe
    Dichiarante, Valentina
    Betti, Cecilia
    Fagnoni, Maurizio
    Maia, Angelamaria
    Landini, Dario
    Albini, Angelo
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (06) : 1834 - 1841
  • [6] Cyanuric chloride as a mild and active Beckmann rearrangement catalyst
    Furuya, Y
    Ishihara, K
    Yamamoto, H
    [J]. 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
    Gui, JZ
    Deng, YQ
    Hu, ZD
    Sun, ZL
    [J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2681 - 2683
  • [9] Clean Beckmann rearrangement of cyclohexanone oxime in caprolactam-based Bronsted acidic ionic liquids
    Guo, S
    Du, ZY
    Zhang, SG
    Li, DM
    Li, ZP
    Deng, YQ
    [J]. GREEN CHEMISTRY, 2006, 8 (03) : 296 - 300
  • [10] Anion nucleophilicity in ionic liquids: a comparison with traditional molecular solvents of different polarity
    Landini, D
    Maia, A
    [J]. TETRAHEDRON LETTERS, 2005, 46 (23) : 3961 - 3963
12