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- Title
[Difluoro(pyridinyl)methyl]phosphonates.
- Authors
Shavrina, Oksana M.; Onys'ko, Petro P.; Rassukana, Yuliya V.
- Abstract
An efficient and convenient method for the synthesis of all isomeric [difluoro(pyridinyl)methyl]phosphonates based on electrophilic fluorination of the corresponding (pyridinylmethyl)phosphonates with N-fluorobenzenesulfonimide has been developed. Hydrolysis and subsequent catalytic hydrogenation of the obtained [difluoro(pyridinyl)methyl]phosphonates afford the respective piperidine-containing α-, β-, and γ-aminophosphonic acids. Thermally unstable diethyl [difluoro(pyridin-4-yl)methyl]phosphonate undergoes O–N transfer of ethyl group to give the corresponding betaine. Hydrolysis of the latter affords 4-[difluoro(phosphono)methyl]-1-ethylpyridin-1-ium salt.
- Subjects
PHOSPHONATES; BETAINE; CATALYTIC hydrogenation; CATALYTIC hydrolysis; ETHYL group; FLUORINATION
- Publication
Chemistry of Heterocyclic Compounds, 2023, Vol 59, Issue 6/7, p415
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-023-03210-1