%0 Journal Article %A Chalyk, Bohdan A. %A Khutorianskyi, Andrii %A Lysenko, Andrii %A Fil, Yulia %A Kuchkovska, Yuliya O. %A Gavrilenko, Konstantin S. %A Bakanovych, Iulia %A Moroz, Yurii S. %A Gorlova, Alina O. %A Grygorenko, Oleksandr O. %D 2019 %T Regioselective Synthesis of Functionalized 3- or 5‑Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles %U https://acs.figshare.com/articles/journal_contribution/Regioselective_Synthesis_of_Functionalized_3-_or_5_Fluoroalkyl_Isoxazoles_and_Pyrazoles_from_Fluoroalkyl_Ynones_and_Binucleophiles/10274816 %R 10.1021/acs.joc.9b02258.s001 %2 https://acs.figshare.com/ndownloader/files/18601622 %K alkyl-substituted isoxazole %K building blocks %K heterocyclic moiety %K fluoroalkyl substituents %K Functionalized 3- %K side chain %K utility %K Regioselective Synthesis %K introduction %K Isocarboxazid %K 5- fluoroalkyl-substituted isoxazoles %K Binucleophile %K isosteric replacement %K multigram scale %K Pyrazole %K scope %K Mepiprazole analogues %K approach %K transformation %K Isoxazole %K molecule %K functionalization site %K pyrazole %K incorporation %K Fluoroalkyl Ynones %K fluoroalkyl-substituted azoles %K synthesis %X A facile synthetic route toward either 3- or 5-fluoroalkyl-substituted isoxazoles or pyrazoles containing an additional functionalization site was developed and applied on a multigram scale. The elaborated approach extends the scope of fluoroalkyl substituents for introduction into the heterocyclic moiety, and uses convenient transformations of the side chain for incorporation of fluoroalkyl-substituted azoles into the structures of biologically active molecules. The utility of the obtained building blocks for isosteric replacement of alkyl-substituted isoxazole and pyrazole was shown by the synthesis of fluorinated Isocarboxazid and Mepiprazole analogues. %I ACS Publications