2-(Trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization

被引:54
作者
Keller, H [1 ]
Schlosser, M [1 ]
机构
[1] UNIV LAUSANNE,INST CHIM ORGAN,CH-1015 LAUSANNE,SWITZERLAND
关键词
D O I
10.1016/0040-4020(96)00168-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Deprotonation of N-ethylidene-tert-butylamine with lithium diisopropylamide and subsequent condensation with ethyl trifluoroacetate gives 4-tert-butylamino-1,1,1-trifluorobut-3-en-2-one. An exchange of the amino substituent occurs when the latter compound is treated with anilines under mildly acidic conditions. When heated in the presence of phosphoryl trichloride, the resulting 4-amino-1,1,1-trifluorobut-3-en-2-ones undergo an N --> ortho shift of the side chain followed by cyclization and dehydration to afford 2-(trifluoromethyl)quinolines.
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页码:4637 / 4644
页数:8
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