Synthesis of 4-(1-alkenyl)isoquinolines by palladium(II)-catalyzed cyclization/olefination

Synthesis of 4-(1-alkenyl)isoquinolines by palladium(II)-catalyzed cyclization/olefination
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DOI:
10.1021/jo0261303
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发表时间:
2003-02-07
影响因子:
3.6
通讯作者:
Larock, RC
Larock, RC
中科院分区:
化学2区
文献类型:
--
作者:
Huang, QH;Larock, RC

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在Pd(II)催化下,2-(1-炔基)芳醛亚胺在各种烯烃存在下环化,以中等至优异的产率合成了各种4-(1-烯基)-3-芳基异喹啉。在芳醛亚胺上引入邻甲氧基促进Pd催化的环化反应并稳定所得Pd(II)中间体,从而提高异喹啉产物的产率。当使用不饱和醇作为烯烃时,含酮异喹啉36和49-51也已通过该方法制备。
A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.