An efficient method for the prepn. of 4-​oxo-​2,​5-​hexadienoates starting from 3,​5-​disubstituted Δ2-​isoxazolines is described. The N-​O bond cleavage of the isoxazoline ring, promoted by molybdenum hexacarbonyl, afforded the β-​hydroxy ketone intermediates (E)​-​4-​R1C6H4CH:CHCOCH2CH(OH)​CO2R (R = Me, Et; R1 = H, NO2, Me, OMe) which were smoothly dehydrated to the expected 4-​oxo-​2,​5-​hexadienoates (E,​E)​-​4-​R1C6H4CH:CHCOCH:CHCO2R in about 40​% yields.

An effect synthesis of 4-oxo-2,5-hexadienoates via D2-isoxazoline intermediates

BARALDI, Pier Giovanni;MANFREDINI, Stefano;SIMONI, Daniele;
1993

Abstract

An efficient method for the prepn. of 4-​oxo-​2,​5-​hexadienoates starting from 3,​5-​disubstituted Δ2-​isoxazolines is described. The N-​O bond cleavage of the isoxazoline ring, promoted by molybdenum hexacarbonyl, afforded the β-​hydroxy ketone intermediates (E)​-​4-​R1C6H4CH:CHCOCH2CH(OH)​CO2R (R = Me, Et; R1 = H, NO2, Me, OMe) which were smoothly dehydrated to the expected 4-​oxo-​2,​5-​hexadienoates (E,​E)​-​4-​R1C6H4CH:CHCOCH:CHCO2R in about 40​% yields.
Baraldi, Pier Giovanni; Bazzanini, Rita; Bigoni, Angelica; Manfredini, Stefano; Simoni, Daniele; Spalluto, Giampiero
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/460441
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