Use of quinolinium salts in parallel synthesis for the preparation of 4-amino-2-alkyl-1,2,3,4-tetrahydroquinoline

被引:21
作者
Bazin, M [1 ]
Kuhn, C [1 ]
机构
[1] Pfizer Global Res & Dev, Dept Chem, Res Technol Ctr, Cambridge, MA 02139 USA
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2005年 / 7卷 / 02期
关键词
D O I
10.1021/cc0498534
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Compounds of pharmacological interest containing a 4-amino-2-alkyl-1,2,3,4-tetrahydroquinoline core structure were prepared starting from 4-chloroquinoline. This has been executed both in solution with a 1-benzyl-4-chloroquinolinium salt and on a solid support with a 1-(4-benzyloxybenzyl-PS)-4-chloroquinolinium resin as key intermediates. Diversification of such intermediates was accomplished through N-arylation of position 4 and subsequent nucleophilic addition of Grignard reagents of position 2 to deliver the expected 4-amino-2-alkyl-1,2,3,4-tetrahydroquinolines in 20-60% yields. The methods described within clearly demonstrate that the quinolinium salts are very efficient intermediates for parallel synthesis.
引用
收藏
页码:302 / 308
页数:7
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