Efficient construction of tri- and tetracyclic heterocycles from linear 1,6-dienes by a domino reaction
Efficient construction of tri- and tetracyclic heterocycles from linear 1,6-dienes by a domino reaction
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DOI：
10.1002/chem.200702035
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发表时间：
2008-01-01
影响因子：
4.3
通讯作者：
Wang, Shaowu
中科院分区：
文献类型：
--
作者：
Hu, Yimin;Song, Fengfa;Wang, Shaowu
含丙烯基线性1，6-二烯与芳基卤化物通过C-C偶联和芳香族C-H官能化，在钯催化下发生多米诺骨牌反应，构建了三环和四环杂环体系。已证明三种不同的丙烯酰胺对该反应非常活跃。芳基卤化物上的取代基可以是乙氧羰基、酮基、氯、磺酰基、氰基等。因此，原料的易得性、底物包括二烯和芳基卤化物的广泛兼容性以及该工艺的一般性使该反应具有很高的价值，因为这些杂环具有合成和医药价值。
Tri- and tetracyclic heterocycle systems were constructed by a palladium-catalyzed domino reaction of linear 1,6-dienes that contain acryl groups with aryl halides through C-C coupling and aromatic C-H functionalization. Three different acrylamides have been shown to be very active for the reaction. The substituents on the aryl halides could be ethoxycarbonyl, ketyl, chloro, sulfonyl, cyano, etc. Thus, the ready accessibility of the starting materials, the wide range of compatibility of substrates including both dienes and aryl halides, and the generality of this process make the reaction highly valuable in view of the synthetic and medicinal importance of these kinds of heterocycles.