Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction
Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction
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DOI：
10.1021/acs.joc.5b00222
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发表时间：
2015-05-15
影响因子：
3.6
通讯作者：
Castagnolo, Daniele
中科院分区：
文献类型：
--
作者：
Chachignon, Helene;Scalacci, Nicolo;Castagnolo, Daniele
丙叉胺与乙基乙烯基醚的Enyne交叉易位反应使取代吡咯的一锅合成成为可能。在微波辐射下，合成了一系列含烷基、芳基和杂芳基的取代吡咯，产率较高。这些反应快速且操作简单，也代表了合成具有挑战性的1，2，3-取代吡咯的简便途径。吡咯转化为3-甲基吡咯和歧化反应产生的3-甲基取代基的衍生化进一步证实了该方法的价值。
Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the method, ology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.