FUNCTIONALIZATION IN POSITION-3 OF 3,5-DICHLORO-2H-1,4-OXAZIN-2-ONES

被引:10
作者
VANAKEN, KJ [1 ]
MEERPOEL, L [1 ]
HOORNAERT, GJ [1 ]
机构
[1] KATHOLIEKE UNIV LEUVEN,DEPT CHEM,CELESTIJNENLAAN 200F,B-3001 LOUVAIN,BELGIUM
关键词
2H-1,4-OXAZIN-2-ONES; CYCLIC IMIDOYL CHLORIDE; ELECTROPHILIC CATALYSIS; DIELS-ALDER REACTION; PYRIDINES;
D O I
10.1016/S0040-4039(00)79064-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrophilic catalysis is shown to give selective substitution of the imidoyl chloride group in 3,5-dichloro-2H-1,4-oxazin-2-ones, avoiding competitive reactions of the nucleophile with the lactone function. With other nucleophiles (SCN-, CH2N2) cyclisations involving the azadiene- or the imine function take place. Cycloaddition of the obtained oxazinones to acetylenic compounds provides polyfunctionalized pyridines.
引用
收藏
页码:2713 / 2716
页数:4
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