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