Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes.
Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes.
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DOI：
10.1021/jo3027033
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发表时间：
2013-01
期刊：
影响因子：
--
通讯作者：
M. Read;L. Gundersen
中科院分区：
文献类型：
--
作者：
M. Read;L. Gundersen
报道了一种新颖有效的菲啶和氮杂类似物的合成方法。关键步骤是微波介导的邻呋喃基（烯丙基氨基）芳烃分子内Diels-Alder环化反应。在催化量的酸存在下，DA-加合物进一步反应得到二氢菲啶，其可以容易地在UV光存在下通过空气或通过DDQ氧化成完全芳族化合物。
A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.