Metal catalyzed multicomponent syntheses of secondary propargylamides and oxazoles from silylimines, acid chlorides, and alkynes

被引：33

作者：

Black, DA ^{[1
]}

Arndtsen, BA ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

TETRAHEDRON | 2005年 / 61卷 / 48期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alkynes; oxazoles; multicomponent;

D O I：

10.1016/j.tet.2005.09.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) and zinc(II) catalyzed routes to construct secondary propargylamides in one-pot procedures from aldehydes, LiN(TMS)(2), acid chlorides, and alkynes are described. This reaction has been subsequently used to provide a one-pot synthesis of oxazoles from four simple building blocks. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：11317 / 11321

页数：5

相关论文

共 47 条

[1] Preparation of 2,5-disubstituted oxazoles from N-propargylamides [J].

Arcadi, A ;

Cacchi, S ;

Cascia, L ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2001, 3 (16) :2501-2504

[2] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[3]

Beller M, 2000, ANGEW CHEM INT EDIT, V39, P1010, DOI 10.1002/(SICI)1521-3773(20000317)39:6<1010::AID-ANIE1010>3.0.CO

[4]

2-P

[5] Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides [J].

Black, DA ;

Arndtsen, BA .

ORGANIC LETTERS, 2004, 6 (07) :1107-1110

[6] ENAMINE CHEMISTRY .1. REACTIONS WITH NONACTIVATED TERMINAL ACETYLENIC COMPOUNDS [J].

BRANNOCK, KC ;

BURPITT, RD ;

THWEATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1462-&

[7] A titanium-catalyzed three-component coupling to generate α,β-unsaturated β-iminoamines [J].

Cao, CS ;

Shi, YH ;

Odom, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2880-2881

[8] An efficient synthesis of N-unsubstituted imines as organoborane adducts stable at room temperature:: New promising intermediates for synthesis [J].

Chen, GM ;

Brown, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4217-4218

[9]

CORNFORTH JW, 1957, HETEROCYCL COMPOUNDS, P298

[10]

DAHLBOM R, 1981, CHOLINERGIC MECHANIS, P621

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