Regioselective Synthesis of Functionalized 3- or 5‑Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles Bohdan A. Chalyk Andrii Khutorianskyi Andrii Lysenko Yulia Fil Yuliya O. Kuchkovska Konstantin S. Gavrilenko Iulia Bakanovych Yurii S. Moroz Alina O. Gorlova Oleksandr O. Grygorenko 10.1021/acs.joc.9b02258.s004 https://acs.figshare.com/articles/dataset/Regioselective_Synthesis_of_Functionalized_3-_or_5_Fluoroalkyl_Isoxazoles_and_Pyrazoles_from_Fluoroalkyl_Ynones_and_Binucleophiles/10274825 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. 2019-11-08 14:45:19 alkyl-substituted isoxazole building blocks heterocyclic moiety fluoroalkyl substituents Functionalized 3- side chain utility Regioselective Synthesis introduction Isocarboxazid 5- fluoroalkyl-substituted isoxazoles Binucleophile isosteric replacement multigram scale Pyrazole scope Mepiprazole analogues approach transformation Isoxazole molecule functionalization site pyrazole incorporation Fluoroalkyl Ynones fluoroalkyl-substituted azoles synthesis