6-nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-SNAr reaction

被引：13
作者：
Bunce, Richard A. [1 ]
Nago, Takahiro [1 ]
机构：
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 04期
关键词：
D O I：
10.1002/jhet.5570450433
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A tandem reductive amination-SNAr reaction has been developed for the synthesis of 6-nitro-1,2,3,4-tetrahydroquinolines. Treatment of 4-(2-fluoro-5-nitrophenyl)-2-butanone or 3-(2-fluoro-5-nitrophenyl)propanal with primary amines and sodium cyanoborohydride in methanol at room temperature provided good to excellent yields of the substituted tetrahydroquinolines. The reaction proceeded best with the ketone substrate using primary amines that were unbranched at the alpha-carbon. The aldehyde also produced the target heterocycles, but these were accompanied by 10-15% of the uncyclized side chain reductive amination products.
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收藏
页码：1155 / 1160
页数：6
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