A convenient one-pot preparative method for 4,5-diarylisoxazoles involving amine exchange reactions

被引:83
作者
Dominguez, E
Ibeas, E
deMarigorta, EM
Palacios, JK
SanMartin, R
机构
[1] Kimika Organikoa Saila, Euskal Herriko Unibertsitatea, 48080 Bilbo
关键词
D O I
10.1021/jo960024h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4,5-Diarylisoxazoles 1 are efficiently prepared by submitting enaminones 2, readily obtained from deoxybenzoins 3, to oximation conditions. This conversion implies an uncommon amine group exchange reaction. Preparation of 4-isoxazolines 5 and ring-opening transformations to beta-keto nitriles 4 and 1,3-amino alcohol derivatives 7 are also described.
引用
收藏
页码:5435 / 5439
页数:5
相关论文
共 71 条
[31]  
HOUSE HO, 1969, J ORG CHEM, P1430
[32]  
JAGER V, 1983, B SOC CHIM BELG, V92, P1039
[33]   SYNTHESES WITH ISOXAZOLINES .9. MODEL REACTIONS FOR THE STEREO-CONTROLLED SYNTHESIS OF AMINOPOLYOLS - REDUCTION OF ISOXAZOLINES WITH FREE OR PROTECTED HYDROXY-GROUPS IN POSITION-4 OR IN SIDE-CHAINS [J].
JAGER, V ;
SCHWAB, W ;
BUSS, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (6-7) :601-603
[34]  
JEON HB, 1993, TETRAHEDRON LETT, V34, P1939
[35]   REACTION OF DIPHENYLCYCLOPROPENONE WITH PYRIDINIUM N-IMINE IN PROTIC MEDIA - QUENCHING OF A REACTIVE INTERMEDIATE [J].
KASCHERES, A ;
MARCHI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (20) :2985-2987
[36]  
KEVILL DN, 1978, TETRAHEDRON LETT, P949
[37]   RECENT DEVELOPMENTS IN ISOXAZOLE CHEMISTRY [J].
KOCHETKOV, NK ;
SOKOLOV, SD .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1963, 2 :365-422
[39]   THE ISOXAZOLINE ROUTE TO THE MOLECULES OF NATURE [J].
KOZIKOWSKI, AP .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (12) :410-416
[40]  
KREBS KG, 1969, THIN LAYER CHROMATOG, P873