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 journalArticle

22 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

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Cyclization
Magnesium
Esters
2-pyrone

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel synthesis of 4-halo-3-hydroxy-2-pyrone : One pot rearrangement- cyclization reaction by magnesium halide. / Komiyama, Takuzo; Takaguchi, Yutaka; Gubaidullin, Aider T.; Mamedov, Vakhid A.; Litvinov, Igor A.; Tsuboi, Sadao.

In: Tetrahedron, Vol. 61, No. 9, 28.02.2005, p. 2541-2547.

Research output: Contribution to journalArticle

Komiyama, Takuzo ; Takaguchi, Yutaka ; Gubaidullin, Aider T. ; Mamedov, Vakhid A. ; Litvinov, Igor A. ; Tsuboi, Sadao. / Novel synthesis of 4-halo-3-hydroxy-2-pyrone : One pot rearrangement- cyclization reaction by magnesium halide. In: Tetrahedron. 2005 ; Vol. 61, No. 9. pp. 2541-2547.
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