Synthesis of 3-phenyl-5-(trifluoromethyl)isoxazole and 5-phenyl-3-(trifluoromethyl)isoxazole

被引：14
|
作者：
Pavlik, JW [1 ]
Lowell, JA [1 ]
Ervithayasuporn, V [1 ]
机构：
[1] Worcester Polytech Inst, Dept Chem & Biochem, Worcester, MA 01609 USA
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2005年 / 42卷 / 07期
关键词：
D O I：
10.1002/jhet.5570420702
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of 4,4,4-trifluoro-1-phenyl-1,3-butanedione with hydroxylamine led to the formation of 5-hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole which was dehydrated to 3-phenyl-5-(trifluoromethyl)isoxazole. This isomer can also be synthesized by reaction of 4-chloro-4-phenyl-1,1,1-trifluoro-3-buten-2-one with sodium azide. The regioisomer, 5-phenyl-3-(trifluoromethyl)isoxazole was synthesized by reaction of 1,1,1-trifluoro-4-phenylbut-3-yn-2-one with hydroxylamine and by the reaction of 3-chloro-1-phenyl-4,4,4-trifluorobut-2-en-1-one with sodium azide. Both isomers were characterized by mass and NMR spectroscopy.
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收藏
页码：1253 / 1255
页数：3
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