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Regioselective Synthesis of Functionalized 3- or 5‑Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles
journal contribution
posted on 2019-11-08, 14:45 authored by 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. GrygorenkoA 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.
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Keywords
alkyl-substituted isoxazolebuilding blocksheterocyclic moietyfluoroalkyl substituentsFunctionalized 3-side chainutilityRegioselective SynthesisintroductionIsocarboxazid5- fluoroalkyl-substituted isoxazolesBinucleophileisosteric replacementmultigram scalePyrazolescopeMepiprazole analoguesapproachtransformationIsoxazolemoleculefunctionalization sitepyrazoleincorporationFluoroalkyl Ynonesfluoroalkyl-substituted azolessynthesis
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