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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

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 S_N2' displacement and aromatization process.

Original language	English
Pages (from-to)	330-335
Number of pages	6
Journal	Asian Journal of Organic Chemistry
Volume	2
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.201200193
Publication status	Published - 2013 Apr

Keywords

Aromatization
Ceric ammonium nitrate
Nitroallylic acetate
Pyrroles
β-keto esters

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201200193

Cite this

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

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",

author = "Magar, {Dhananjay R.} and Ke, {Yi Jiun} and Kwunmin Chen",

year = "2013",

month = apr,

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language = "English",

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pages = "330--335",

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T1 - Three-component Synthesis of Functionalized N-Protected Tetrasubstituted Pyrroles by an Addition-Elimination-Aromatization Process

AU - Magar, Dhananjay R.

AU - Ke, Yi Jiun

AU - Chen, Kwunmin

PY - 2013/4

Y1 - 2013/4

N2 - 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.

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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DO - 10.1002/ajoc.201200193

M3 - Article

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 4

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 898197: Experimental Crystal Structure Determination

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 898197: Experimental Crystal Structure Determination

Cite this