Novel synthesis of 4-halo-3-hydroxy-2-pyrone: one pot rearrangement–cyclization reaction by magnesium halide
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- 作者：Komiyama ; Takuzo ; Takaguchi ; Yutaka ; Gubaidullin ; Aider T. ; Mamedov ; Vakhid A. ; Litvinov ; Igor A. ; et. al.
- 关键词：3-Hydroxy-2-pyrone ; Magnesium halide ; Darzens condensation ; Dichloroacetate ; Cyclization
- 刊名：Tetrahedron
- 出版年：2005
- 出版时间：February 28, 2005
- 年：2005
- 卷：61
- 期：9
- 页码：2541-2547
- 全文大小：308 K
文摘
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.