Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction

被引：38

作者：

Chachignon, Helene ^{[1
]}

Scalacci, Nicolo ^{[1
]}

Petricci, Elena ^{[2
]}

Castagnolo, Daniele ^{[1
]}

机构：

[1] Northumbria Univ Newcastle, Dept Appl Sci, Newcastle Upon Tyne NE1 8ST, Tyne & Wear, England

[2] Univ Siena, Dipartimento Biotecnol Chim & Farm, I-53100 Siena, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 10期

关键词：

RING-CLOSING METATHESIS; MULTICOMPONENT REACTIONS; SUBSTITUTION-REACTIONS; CYCLOISOMERIZATION; HETEROCYCLES; AROMATIZATION; DERIVATIVES; INHIBITORS; ALDEHYDES; CATALYSTS;

D O I：

10.1021/acs.joc.5b00222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5287 / 5295

页数：9

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