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

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.

Treatment of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester 1 with magnesium halides gave 4-halo-3-hydroxy-2-pyrone 2 in excellent to reasonable yields in one pot. The mechanism of this novel rearrangement-cyclization reaction is also proposed.Figure optionsDownload as PowerPoint slide