Synthetic Approaches to Fluorinated Derivatives of 4-(vinylthio)pyridine | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthetic Approaches to Fluorinated Derivatives of 4-(vinylthio)pyridine Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2022, Volume: 264, Article number : 110063, Pages count : 9 DOI: 10.1016/j.jfluchem.2022.110063

Tags

Pentafluoropyridine; Aromatic nucleophilic substitution; Fluorinated heterocycles; Pyridyl vinyl sulfide; Pyridyl vinyl sulfone

Authors

Politanskaya Larisa ¹ , Khasanov Bulat ^1,2 , Patapov Alexander ³

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 9, Novosibirsk 630090, Russian Federation
2	Novosibirsk State University, Pirogova Street, 2, Novosibirsk 630090, Russian Federation
3	Boreskov Institute of Catalysis, Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 5, Novosibirsk 630090, Russian Federation

Funding (1)

Ministry of Science and Higher Education of the Russian Federation

FWUE-2022-0002 (122040400035-3)

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.

Politanskaya L. , Khasanov B. , Patapov A.
Synthetic Approaches to Fluorinated Derivatives of 4-(vinylthio)pyridine
Journal of Fluorine Chemistry. 2022. V.264. 110063 :1-9. DOI: 10.1016/j.jfluchem.2022.110063 WOS Scopus РИНЦ AN OpenAlex

Submitted:	Sep 18, 2022
Accepted:	Nov 24, 2022
Published online:	Nov 28, 2022
Published print:	Dec 1, 2022

Web of science:	WOS:000893562800006
Scopus:	2-s2.0-85142740851
Elibrary:	50509241
Chemical Abstracts:	2022:3027220
OpenAlex:	W4310243816

DB	Citing
Scopus	3
Web of science	3
Elibrary	3
OpenAlex	4