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.File in questo prodotto:
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