Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 23, Pages 15212-15225Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02258
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Funding
- Enamine Ltd.
- NIH [GM133836]
- Ministry of Education and Science of Ukraine [19BF37-03]
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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.
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