The intramolecular aromatic electrophilic substitution of aminocyclopropanes prepared by the Kulinkovich-de Meijere reaction
The intramolecular aromatic electrophilic substitution of aminocyclopropanes prepared by the Kulinkovich-de Meijere reaction
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DOI：
10.1002/ejoc.200500428
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发表时间：
2005-10-28
影响因子：
2.8
通讯作者：
Six, Y
中科院分区：
文献类型：
--
作者：
Larquetoux, L;Ouhamou, N;Six, Y
本文介绍了分子内Kulinkovich-de Meijere反应的新实例，该反应应用于在适当位置含有烯烃部分和芳环的羧酸酰胺。加热后，得到的氨基环丙烷经过分子内的芳香族亲电取代得到多环体系。在制备的各种起始原料中，吲哚和苯酚的衍生物得到了最好的结果。在每种情况下，在新形成的环结处引入了一个苄基四元中心。在一个例子中，使用催化量的对甲苯磺酸极大地提高了环化效率。
This article describes new examples of intramolecular Kulinkovich-de Meijere reactions applied to carboxylic amides bearing an olefin moiety and an aromatic ring at a suitable position. Upon heating, the aminocyclopropanes thus obtained undergo intramolecular aromatic electrophilic substitution to afford polycyclic systems. Among the various starting materials prepared, best results are obtained from indole and phenol derivatives. In each case, a benzylic quaternary centre is introduced at the newly-formed ring junction. On one example, the efficiency of the cyclisation has been dramatically improved using a catalytic amount of para-toluenesulfonic acid.