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Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles.

ABSTRACT: 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.

SUBMITTER: Chalyk BA

PROVIDER: S-EPMC7310498 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles.

Chalyk Bohdan A BA Khutorianskyi Andrii A Lysenko Andrii A Fil Yulia Y Kuchkovska Yuliya O YO Gavrilenko Konstantin S KS Bakanovych Iulia I Moroz Yurii S YS Gorlova Alina O AO Grygorenko Oleksandr O OO

The Journal of organic chemistry 20191108 23

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 buil ...[more]

PMID: 31661620

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