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

Dhananjay R. Magar; Yi Jiun Ke; Kwunmin Chen

doi:10.1002/ajoc.201200193

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

Dhananjay R. Magar, Yi Jiun Ke, Kwunmin Chen

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

34 引文斯高帕斯（Scopus）

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 β-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_N2' displacement and aromatization process.

原文	英語
頁（從 - 到）	330-335
頁數	6
期刊	Asian Journal of Organic Chemistry
卷	2
發行號	4
DOIs	https://doi.org/10.1002/ajoc.201200193
出版狀態	已發佈 - 2013 一月 1

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201200193

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引用此

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abstract = "A three-component, one-pot, synthesis of N-protected tetrasubstituted pyrroles has been developed by treating nitroallylic acetates with an amine and a β-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 SN2' displacement and aromatization process.",

keywords = "Aromatization, Ceric ammonium nitrate, Nitroallylic acetate, Pyrroles, β-keto esters",

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AB - A three-component, one-pot, synthesis of N-protected tetrasubstituted pyrroles has been developed by treating nitroallylic acetates with an amine and a β-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 SN2' displacement and aromatization process.

KW - Aromatization

KW - Ceric ammonium nitrate

KW - Nitroallylic acetate

KW - Pyrroles

KW - β-keto esters

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