Novel synthesis of 4-halo-3-hydroxy-2-pyrone: One pot rearrangement- cyclization reaction by magnesium halide

Takuzo Komiyama, Yutaka Takaguchi, Aider T. Gubaidullin, Vakhid A. Mamedov, Igor A. Litvinov, Sadao Tsuboi

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Treatment of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester or its rearrangement product, the acetonide protected 4,5-dihydroxy-3-chloro-2-oxo ester, with magnesium halides gave 4-halo-3-hydroxy-2-pyrone in excellent to reasonable yields in one pot. The mechanism of this novel one pot rearrangement-cyclization reaction is also proposed.

Original languageEnglish
Pages (from-to)2541-2547
Number of pages7
JournalTetrahedron
Volume61
Issue number9
DOIs
Publication statusPublished - Feb 28 2005

Keywords

  • 3-Hydroxy-2-pyrone
  • Cyclization
  • Darzens condensation
  • Dichloroacetate
  • Magnesium halide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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