Three-component Synthesis of Functionalized N-Protected Tetrasubstituted Pyrroles by an Addition-Elimination-Aromatization Process

被引：37

作者：

Magar, Dhananjay R. ^{[1
]}

Ke, Yi-Jiun ^{[1
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2卷 / 04期

关键词：

aromatization; beta-keto esters; ceric ammonium nitrate; nitroallylic acetate; pyrroles; BAYLIS-HILLMAN REACTION; BETA-ENAMINO KETONES; EFFICIENT SYNTHESIS; POLYSUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRROLES; VINYL AZIDES; ONE-POT; NITROALLYLIC ACETATES; DERIVATIVES;

D O I：

10.1002/ajoc.201200193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-component, one-pot, synthesis of N-protected tetrasubstituted pyrroles has been developed by treating nitroallylic acetates with an amine and a beta-keto ester mediated by ceric ammonium nitrate in MeOH. By this method, a diverse array of N-protected pyrrole 2,4-dicarboxylic acid derivatives have been synthesized in 37-76% yield. The reactions proceed smoothly through an interesting S(N)2' displacement and aromatization process.

引用

页码：330 / 335

页数：6

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