Cascade Formation of Isoxazoles: Facile Base-Mediated Rearrangement of Substituted Oxetanes

被引：67
作者：
Burkhard, Johannes A. [1 ]
Tchitchanov, Boris H. [1 ]
Carreira, Erick M. [1 ]
机构：
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 23期
关键词：
aldehydes; heterocycles; nitro compounds; oxetanes; rearrangements; COPPER(I)-CATALYZED SYNTHESIS; CYCLOADDITION ROUTE; PRACTICAL SYNTHESIS; BUILDING-BLOCKS; DRUG DISCOVERY; NITRILE OXIDES; OXETAN-3-ONES; REACTIVITY;
D O I：
10.1002/anie.201100260
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5379 / 5382
页数：4
相关论文
共 52 条
[1]  
ALBERT R, 2009, Patent No. 2009068682
[2]  
[Anonymous], 2010, ANGEW CHEM
[3]   Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].
Aschwanden, P ;
Frantz, DE ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (15) :2331-2333
[4]   Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring [J].
Balsamo, A ;
Coletta, I ;
Guglielmotti, A ;
Landolfi, C ;
Mancini, F ;
Martinelli, A ;
Milanese, C ;
Minutolo, F ;
Nencetti, S ;
Orlandini, E ;
Pinza, M ;
Rapposelli, S ;
Rossello, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (02) :157-168
[5]  
Barlaam B. C., 2009, PCT Int. Appl., Patent No. [2009024825, WO2,009,024,825]
[6]  
Bergeron P., 2010, PCT Int. Appl., Patent No. [WO2010014939, 2010014939]
[7]   Simple synthesis of symmetrical 4-substituted 3,5-dialkylisoxazoles [J].
Best, WM ;
Ghisalberti, EL ;
Powell, M .
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (07) :388-+
[8]  
Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO
[9]  
2-1
[10]  
BODE JW, 2001, ANGEW CHEM, V113, P2128
123456