Microwave-Assisted Beckmann Rearrangement of Aryl Ketoximes Catalyzed by In(OTf)3 in Ionic Liquid

被引：16
作者：
Sugamoto, Kazuhiro [1 ]
Matsushita, Yoh-ichi [1 ]
Matsui, Takanao [1 ]
机构：
[1] Miyazaki Univ, Fac Engn, Dept Appl Chem, Miyazaki 8892192, Japan
来源：
SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 06期
关键词：
Beckmann rearrangement; In(OTf)3; ionic liquid; microwave; MEDIATED ZINC-CHLORIDE; EFFICIENT CATALYST; FACILE CONVERSION; ACID; AMIDES; DEHYDRATION; IRRADIATION; CAPROLACTAM; OXIMES;
D O I：
10.1080/00397911003707063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[image omitted] Beckmann rearrangement of aryl ketoximes catalyzed by In(OTf)3 gave amides in ionic liquid under microwave irradiation. Aryl ketoximes were converted to corresponding amides in good yield within very short times (10-270s). The catalyst and the ionic liquid were easily recovered and reused.
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收藏
页码：879 / 884
页数：6
相关论文
共 19 条
[1]   Indium-mediated facile dehydration and Beckmann rearrangement of grimes [J].
Barman, DC ;
Thakur, AJ ;
Prajapati, D ;
Sandhu, JS .
CHEMISTRY LETTERS, 2000, (10) :1196-1197
[2]   RuCl3 catalyzed facile conversion of arylalkyl ketoximes to amides [J].
De, SK .
SYNTHETIC COMMUNICATIONS, 2004, 34 (18) :3431-3434
[3]  
De SK, 2004, J CHEM RES, P131
[4]   Synthesis of N-alkylimidazolium salts and their utility as solvents in the Beckmann rearrangement [J].
Elango, Kandasamy ;
Srirambalaji, Renganathan ;
Anantharaman, Ganapathi .
TETRAHEDRON LETTERS, 2007, 48 (51) :9059-9062
[5]   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
[6]   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
[7]   Environmentally friendly Beckmann rearrangement of oximes catalyzed by metaboric acid in ionic liquids [J].
Guo, S ;
Deng, YQ .
CATALYSIS COMMUNICATIONS, 2005, 6 (03) :225-228
[8]   Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst [J].
Hashimoto, Masaharu ;
Obora, Yasushi ;
Sakaguchi, Satoshi ;
Ishii, Yasutaka .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2894-2897
[9]   Thermal behaviors of ionic liquids under microwave irradiation and their application on microwave-assisted catalytic Beckmann rearrangement of ketoximes [J].
Lee, JK ;
Kim, DC ;
Song, CE ;
Lee, SG .
SYNTHETIC COMMUNICATIONS, 2003, 33 (13) :2301-2307
[10]   Highly efficient Beckmann rearrangement and dehydration of oximes [J].
Li, DM ;
Shi, F ;
Guo, S ;
Deng, YQ .
TETRAHEDRON LETTERS, 2005, 46 (04) :671-674
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