Isoxazolinoisoquinoline heterocycles via solid-phase Reissert and Suzuki reactions

被引:61
作者
Lorsbach, BA [1 ]
Bagdanoff, JT [1 ]
Miller, RB [1 ]
Kurth, MJ [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
D O I
10.1021/jo9720142
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A traceless solid-phase synthesis strategy has been developed that delivers novel isoxazolinoisoquinoline heterocycles. The process consists of solid-phase Reissert formation (isoquinoline --> I), Suzuki coupling lithiation, and subsequent C1-alkylation (I --> II), and exo-olefin selective 1,3-dipolar nitrile oxide cycloaddition followed by Reissert; hydrolysis (II --> III) to liberate the targeted heterocycle.
引用
收藏
页码:2244 / 2250
页数:7
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