Approaches for the introduction of fluorinated substituents into [1,2,3]Triazolo[1,5-a]pyridines

•Novel trifluoromethyl triazolopyridines have been synthesized.•Trifluoromethylated pyridines have been obtained from triazolopyridines.•A fluorine mediated triazolopyridine dimerization was found.•Imidazo[1,5-a]pyridines have been synthesized from triazolopyridines by reaction of this heterocycles with Selectfluor.

[1,2,3]Triazolo[1,5-a]pyridines functionalization with a trifluoromethyl group has been achieved for the first time using different synthetic strategies. Furthermore, these scaffolds have been employed as starting material in the synthesis of new 2,6-disubstituted pyridines containing the trifluoromethyl group, compounds that are not available using other methodologies. A fluorine-mediated triazolopyridine dimerisation is described, improving the previously known synthetic method. Preliminary studies focused on exploring triazolopyridines reactivity with electrophilic fluorine have revealed a new approach for the obtainment of imidazopyridines.

Graphical abstractSeveral approaches aimed at the fluorination of [1,2,3]triazolo[1,5-a]pyridines have been explored. Novel trifluoromethyl substituted pyridines have been synthesized from triazolopyridines. Fluorination attempts have yielded two new synthetic routes for the obtention of triazolopyridines dimers and imidazo[1,5-a]pyridines.Figure optionsDownload full-size imageDownload as PowerPoint slide