Monatshefte fur Chemie p. 727 - 738 (1988)
Update date:2022-09-26
Topics:
Kappe, Thomas
Wildpanner, Hans
Fused 2-pyrones 4, obtained by the thermal condensation of ketones 1 with reactive malonates 2, rearrange above 200 deg C to yield condensed dihydroxynaphthalines 5.The latter compounds can be oxidized to give 3-hydroxy-1,4-naphthoquinone-5-alkanoic acids.The reaction of ketone 8 with magic malonates 2 or chlorocarbonyl ketene 9 affords the pyrones 11 in low yields.The 2-pyrones 11 could not be rearranged to 13; a possible explanation for this behaviour is presented. - Keywords: Trichlorophenyl malonates; 2-Pyrone synthesis; Carbonyl ketenes as intermediates; Hydroxy-1,4-naphthoquinone alkanoic acids
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