An Efficient Synthesis of N-Substituted-3-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)propanamides by Four-Component Reaction in Aqueous Medium

被引：3

作者：

Dou, Guo-Lan ^{[1
]}

Wang, De-Ming ^{[1
]}

Zhong, Xiao-Xing ^{[1
]}

Shi, Da-Qing ^{[2
]}

机构：

[1] China Univ Min & Technol, Sch Safety Engn, Xuzhou 221116, Peoples R China

[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2013年 / 50卷 / 01期

关键词：

ONE-POT SYNTHESIS; DIELS-ALDER REACTIONS; AMIDE BOND FORMATION; 3-COMPONENT REACTION; MULTICOMPONENT REACTIONS; CLAISEN REARRANGEMENT; CATALYZED SYNTHESIS; COUPLING REAGENTS; CARBON-MONOXIDE; DERIVATIVES;

D O I：

10.1002/jhet.1000

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient synthesis of N-substituted-3-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)propanamides via four-component reaction of an aldehyde, amine, Meldrum's acid, and 4-hydroxy-6-methyl-2H-pyran-2-one 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 begin environmentally friendly.

引用

页码：99 / 103

页数：5

共 63 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

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