One-pot synthesis of oxazoles using isocyanide surrogates

被引:24
作者
El Kaim, Laurent [1 ]
Grimaud, Laurence [1 ]
Schiltz, Aurelie [1 ]
机构
[1] Ecole Natl Super Tech Avancees, Lab Chim & Procedes, DCSO, UMR 7652, F-75015 Paris, France
关键词
Isocyanide; Oxazole; Alkylation; Silver cyanide; Multicomponent reaction; ALKYL-HALIDES; ISONITRILE;
D O I
10.1016/j.tetlet.2009.07.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We wish to present herein a simple one-pot synthesis of 2,5-disubstituted oxazoles, starting from benzyl halides and acyl chlorides. The in Situ formation of isocyanides, followed by the addition of an acyl chloride in the presence of a base leads to the desired oxazoles in good yields. (C) 2009 Published by Elsevier Ltd.
引用
收藏
页码:5235 / 5237
页数:3
相关论文
共 21 条
[1]  
Anastas P., 1998, GREEN CHEM THEORY PR
[2]   Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones [J].
Bonne, Damien ;
Dekhane, Mouloud ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2485-2488
[3]   Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones [J].
Clarke, Paul A. ;
Santos, Soraia ;
Martin, William H. C. .
GREEN CHEMISTRY, 2007, 9 (05) :438-440
[4]   Unconventional oxazole formation from isocyanides [J].
dos Santos, Aurelie ;
El Kaim, Laurent ;
Grimaud, Laurence ;
Ronsseray, Caroline .
CHEMICAL COMMUNICATIONS, 2009, (26) :3907-3909
[5]   Isocyanide-Based Multicomponent Reaction 'without' Isocyanides [J].
El Kaim, Laurent ;
Grimaud, Laurence ;
Schiltz, Aurelie .
SYNLETT, 2009, (09) :1401-1404
[6]   Selective formation of 2-imidazolines and 2-substituted oxazoles by using a three-component reaction [J].
Elders, Niels ;
Ruijter, Eelco ;
de Kanter, Frans J. J. ;
Groen, Marinus B. ;
Orru, Romano V. A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4961-4973
[7]  
ELKAIM L, 2009, ORG BIOMOL CHEM
[8]   ISOCYANIDES FROM ALKYL-HALIDES AND ONIUM DICYANOARGENTATES - SCOPE AND MECHANISM [J].
ENGEMYR, LB ;
MARTINSE.A ;
SONGSTAD, J .
ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1974, A 28 (03) :255-266
[9]  
Gokel G.W., 1988, ORG SYNTH, V6, P232
[10]  
HOFFMANN AW, 1867, ANN CHEM PHARM, V144, P114