Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones

A Green and Novel Method for the Synthesis of 4,4‐Difluoro‐3‐oxo‐2‐(triphenylphosphoranylidene) δ‐Lactones by Reformatsky Reaction

“…As shown in Scheme 1, ethyl 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate (1) was easily prepared through the procedure developed by Hamper 12,13 from the reaction of bromodifluoroacetic anhydride with readily available phosphonium salt in high yield. A series of the Reformatsky reaction of compound 1 with benzaldehyde were studied mediated by indium and cuprous chloride in aqueous medium.…”

One-pot synthesis of 4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)-δ-lactones by Reformatsky reaction

“…As shown in Scheme 1, ethyl 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate 1 was easily prepared by the same procedure of Hamper [12] from the reaction of bromodifluoroacetic anhydride [13] with readily available phosphonium salt in 85% yield.…”

“…470 MHz) d À119.9 (1F, d, J F-F = 277 Hz), À124.5 (1F, dd, J F-F = 277 Hz, J F-H = 14 Hz) 13. C NMR (CDCl 3 , 125.8 MHz) d 179.3 ( 2 J CF = 25 Hz), 166.3 ( 2 J CP = 11 Hz), 136.8, 134.5 ( 3 J CP = 10.3 Hz), 133.8, 129.7 ( 3 J CP = 13 Hz), 129.4, 129.2, 127.6, 123.1 ( 1 J CP = 93 Hz), 119.4, 110.1 (CF 2 , 1 J CF = 253 Hz, 3 J CP = 17 Hz), 69.8 ( 1 J CP = 111.5 Hz).…”

Synthesis and in vitro antibacterial activity of novel fluoroalkyl-substituted pyrazolyl oxazolidinones

“…The synthesis of key intermediates 9 is depicted in Scheme 2. b-Ethyloxyvinyl uoroalkyl ketones 5 were prepared from ethyl vinyl ether and its derivatives with uoroalkylacetic anhydride under base condition. 22 Treatment of compounds 5 with pnitrophenylhydrazines 6 in ethanol gave exclusively the 5hydroxy-4,5-dihydropyrazoles 7. Dehydration and reduction of the nitro group afforded the corresponding pyrazoles 9.…”

“…18,19 Many commercial drugs containing trifluoromethyl and difluoromethyl groups have come to market. 22 Treatment of compounds 5 Consequently, we are interested in developing fluoroalkyl-containing oxazolidinones and expect these compounds might result in potent antibacterial activity.…”