A facile synthesis of 2-oxazolines using a PPh3-DDQ system

被引：27

作者：

Xu, Quancai ^{[1
]}

Li, Zhengning ^{[1
,2
]}

机构：

[1] Dalian Univ, Coll Environm & Chem Engn, Dalian 116622, Peoples R China

[2] Dalian Univ, Liaoning Key Lab Bioorgan Chem, Dalian 116622, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 49期

关键词：

2-Oxazoline; Synthesis; DDQ; Triphenylphosphine; POT DIRECT SYNTHESIS; EFFICIENT SYNTHESIS; OXAZOLINES; BIS(OXAZOLINE); CONVERSION; LIGANDS; MILD; ALCOHOLS; AMIDES; 2-IMIDAZOLINES;

D O I：

10.1016/j.tetlet.2009.09.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of 2-oxazolines from N-(2-hydroxyethyl)amides using a triphenylphosphine-2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DQQ) system is described. The reaction proceeds under neutral and mild conditions, and excellent yields are obtained. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6838 / 6840

页数：3

共 40 条

[1] Synthesis and crystallographic characterization of chiral bis-oxazoline-amides. Fine-tunable ligands for Pd-catalyzed asymmetric alkylations [J].

Albano, Vincenzo Giulio ;

Bandini, Marco ;

Monari, Magda ;

Marcucci, Eleonora ;

Piccinelli, Fabio ;

Umani-Ronchi, Achille .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6451-6458

[2] cis-Selective cyclopropanations using chiral 5,5-diaryl bis(oxazoline) catalysts [J].

Alexander, K ;

Cook, S ;

Gibson, CL .

TETRAHEDRON LETTERS, 2000, 41 (36) :7135-7138

[3] Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2003, 44 (11) :2331-2333

[4] Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal [J].

Braga, Antonio L. ;

Galetto, Fabio Z. ;

Taube, Paulo S. ;

Paixao, Marcio W. ;

Silveira, Claudio C. ;

Singh, Devender ;

Vargas, Fabricio .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (24) :3563-3566

[5] Heterogeneous enantioselective catalyzed carbonyl- and imino-ene reactions using copper bis(oxazoline) zeolite Y [J].

Caplan, NA ;

Hancock, FE ;

Page, PCB ;

Hutchings, GJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (13) :1685-1688

[6] Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide [J].

Crosignani, S ;

Young, AC ;

Linclau, B .

TETRAHEDRON LETTERS, 2004, 45 (52) :9611-9615

[7] Concise synthesis of conformationally constrained pybox ligands [J].

Davies, IW ;

Gerena, L ;

Lu, N ;

Larsen, RD ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9629-9630

[8] C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis [J].

Desimoni, Giovanni ;

Faita, Giuseppe ;

Jorgensen, Karl Anker .

CHEMICAL REVIEWS, 2006, 106 (09) :3561-3651

[9] Enantioselective Syn-selective scandium-catalyzed ene reactions [J].

Evans, DA ;

Wu, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8006-8007

[10] Enantioselective Friedel-Crafts alkylations of α-β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].

Evans, DA ;

Fandrick, KR ;

Song, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8942-8943

← 1 2 3 4 →