An Efficient Synthesis of N-Substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propanamides by Four-component Reaction in Aqueous Medium

被引：9
作者：
Dou Guolan [1 ]
Zhong Xiaoxing [1 ]
Wang Deming [1 ]
Shi Daqing [2 ]
机构：
[1] China Univ Min & Technol, Sch Safety Engn, Xuzhou 221116, Jiangsu, Peoples R China
[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Jiangsu, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 11期
关键词：
amide; four-component reaction; aqueous medium; synthetic method; ONE-POT SYNTHESIS; METHYLENE-GAMMA-BUTYROLACTONES; DIELS-ALDER REACTIONS; AMIDE BOND FORMATION; 3-COMPONENT REACTION; MULTICOMPONENT REACTIONS; CLAISEN REARRANGEMENT; CATALYZED SYNTHESIS; COUPLING REAGENTS; CARBON-MONOXIDE;
D O I：
10.1002/cjoc.201180404
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild and efficient synthesis of N-substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propanamides via four-component reaction of an aldehyde, amine, Meldrum's acid and 5,5-dimethylcyclo-hexane-1,3-dione in the presence of benzyltriethylammonium chloride (TEBAC) in aqueous medium is described. This method has the advantages of accessible starting materials, good yields, mild reaction conditions and eco-friendliness.
引用
收藏
页码：2368 / 2372
页数：5
相关论文
共 65 条
[1]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[2]   A novel metal iodide promoted three-component synthesis of substituted pyrrolidines [J].
Bertozzi, F ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2002, 4 (18) :3147-3150
[3]  
Bigenayme H., 2000, CHEM-EUR J, V6, P3321
[4]  
Bode JW, 2006, CURR OPIN DRUG DISC, V9, P765
[5]   A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction [J].
Bora, U ;
Saikia, A ;
Boruah, RC .
ORGANIC LETTERS, 2003, 5 (04) :435-438
[6]  
Brelow R., 1983, TETRAHEDRON LETT, V24, P1901
[7]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[8]   ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
MAITRA, U .
TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240
[9]   Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes [J].
Chang, Joyce Wei Wei ;
Chan, Philip Wai Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1138-1140
[10]   A convenient solution and solid-phase synthesis of Δ5-2-oxopiperazines via N-acyliminium ions cyclization [J].
Cheng, JF ;
Chen, M ;
Arrhenius, T ;
Nadzan, A .
TETRAHEDRON LETTERS, 2002, 43 (36) :6293-6295
1234567