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

Dhananjay R. Magar, Yi Jiun Ke, Kwunmin Chen

Research output: Contribution to journalArticle

32 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 SN2' displacement and aromatization process.

Original languageEnglish
Pages (from-to)330-335
Number of pages6
JournalAsian Journal of Organic Chemistry
Volume2
Issue number4
DOIs
Publication statusPublished - 2013 Jan 1

Keywords

  • Aromatization
  • Ceric ammonium nitrate
  • Nitroallylic acetate
  • Pyrroles
  • β-keto esters

ASJC Scopus subject areas

  • Organic Chemistry

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