Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition

Mei Yuan Hsu, Justin Dietrich, Christopher Hulme, Arthur Y. Shaw

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file.

Original languageEnglish (US)
Pages (from-to)1538-1542
Number of pages5
JournalSynthetic Communications
Volume43
Issue number11
DOIs
StatePublished - Apr 22 2013

Keywords

  • Cyclo-dehydration
  • Dehydrating agent
  • Imidazole-4-carboxylate
  • [3+2] Cycloaddition
  • Δ2-oxazolinone

ASJC Scopus subject areas

  • Organic Chemistry

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