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

doi:10.1016/j.tet.2004.12.037

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 journal › Article › peer-review

25 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 language	English
Pages (from-to)	2541-2547
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	9
DOIs	https://doi.org/10.1016/j.tet.2004.12.037
Publication status	Published - 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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10.1016/j.tet.2004.12.037

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

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.",

keywords = "3-Hydroxy-2-pyrone, Cyclization, Darzens condensation, Dichloroacetate, Magnesium halide",

author = "Takuzo Komiyama and Yutaka Takaguchi and Gubaidullin, {Aider T.} and Mamedov, {Vakhid A.} and Litvinov, {Igor A.} and Sadao Tsuboi",

year = "2005",

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T1 - Novel synthesis of 4-halo-3-hydroxy-2-pyrone

T2 - One pot rearrangement- cyclization reaction by magnesium halide

AU - Komiyama, Takuzo

AU - Takaguchi, Yutaka

AU - Gubaidullin, Aider T.

AU - Mamedov, Vakhid A.

AU - Litvinov, Igor A.

AU - Tsuboi, Sadao

PY - 2005/2/28

Y1 - 2005/2/28

N2 - 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.

AB - 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.

KW - 3-Hydroxy-2-pyrone

KW - Cyclization

KW - Darzens condensation

KW - Dichloroacetate

KW - Magnesium halide

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M3 - Article

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SP - 2541

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JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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