Abstract: Highlights • Directed synthesis of fluorinated 4-(vinylthio)pyridines. • DBU-promoted elimination process. • Valuable building blocks to obtain potentially biologically active fluorinated compounds. Abstract An effective strategy for the synthesis of new polyfluoropyridine derivatives, which are valuable building blocks in the synthesis of potentially biologically active fluorine-containing compounds, has been developed. A series of fluorinated derivatives of 4-(vinylthio)pyridine have been synthesized, starting from pentafluoropyridine and 2-mercaptoethanol via aromatic nucleophilic substitution of fluorine atoms and elimination process. The obtained derivatives with NHAlk-substituents at position 2-, are of interest as new heteroaryl vinyl sulfide components that can be used in the synthesis of more complex fluorine-containing structures. The possibility of oxidation of tetrafluoro-4-(vinylthio)pyridine to the corresponding heteroaryl vinyl sulfone has been demonstrated. It was found that the resulting tetrafluoro-4-(vinylsulfonyl)pyridine reacted with cycloheptanamine under basic conditions to form a heterocyclic framework containing fragments of pyridine and 3,4-dihydro-2H-1,4-thiazine 1,1-dioxide.

Cite: Politanskaya L. , Khasanov B. , Potapov A.
Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine
Journal of Fluorine Chemistry. 2022. V.264. P.110063. DOI: 10.1016/j.jfluchem.2022.110063 WOS РИНЦ

Identifiers:

Web of science	WOS:000893562800006
Elibrary	50509241
OpenAlex	W4310243816

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