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Novel synthesis of 4-halo-3-hydroxy-2-pyrone: one pot rearrangement-cyclization reaction by magnesium halide |
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| Authors: | Takuzo Komiyama Aider T. Gubaidullin Igor A. Litvinov |
| Affiliation: | a Department of Environmental Chemistry and Materials, Faculty of Environmental Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan b A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Science, Arbuzov str. 8, Kazan 420088, Russian Federation |
| 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 Magnesium halide Darzens condensation Dichloroacetate Cyclization |
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