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Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine. / Politanskaya, Larisa; Khasanov, Bulat; Potapov, Alexander.

In: Journal of Fluorine Chemistry, Vol. 264, 110063, 12.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

Politanskaya, L, Khasanov, B & Potapov, A 2022, 'Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine', Journal of Fluorine Chemistry, vol. 264, 110063. https://doi.org/10.1016/j.jfluchem.2022.110063

APA

Politanskaya, L., Khasanov, B., & Potapov, A. (2022). Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine. Journal of Fluorine Chemistry, 264, [110063]. https://doi.org/10.1016/j.jfluchem.2022.110063

Vancouver

Politanskaya L, Khasanov B, Potapov A. Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine. Journal of Fluorine Chemistry. 2022 Dec;264:110063. doi: 10.1016/j.jfluchem.2022.110063

Author

Politanskaya, Larisa ; Khasanov, Bulat ; Potapov, Alexander. / Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine. In: Journal of Fluorine Chemistry. 2022 ; Vol. 264.

BibTeX

@article{00c78d75775f41629d362047c6d4f5d6,
title = "Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine",
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.",
keywords = "Aromatic nucleophilic substitution, Fluorinated heterocycles, Pentafluoropyridine, Pyridyl vinyl sulfide, Pyridyl vinyl sulfone",
author = "Larisa Politanskaya and Bulat Khasanov and Alexander Potapov",
note = "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: {\textcopyright} 2022 Elsevier B.V.",
year = "2022",
month = dec,
doi = "10.1016/j.jfluchem.2022.110063",
language = "English",
volume = "264",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

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 -

ID: 40001084