TY - JOUR

T1 - Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine

AU - Politanskaya, Larisa

AU - Khasanov, Bulat

AU - Potapov, Alexander

N1 - Funding Information: The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and Ministry of Science and Higher Education of the Russian Federation (Project FWUE-2022-0002 ) for financial support. Publisher Copyright: © 2022 Elsevier B.V.

PY - 2022/12

Y1 - 2022/12

N2 - 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.

AB - 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.

KW - Aromatic nucleophilic substitution

KW - Fluorinated heterocycles

KW - Pentafluoropyridine

KW - Pyridyl vinyl sulfide

KW - Pyridyl vinyl sulfone

UR - http://www.scopus.com/inward/record.url?scp=85142740851&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/b722dbda-6b26-34f8-a312-9ebb6a1277a3/

U2 - 10.1016/j.jfluchem.2022.110063

DO - 10.1016/j.jfluchem.2022.110063

M3 - Article

AN - SCOPUS:85142740851

VL - 264

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 110063

ER -