[DIFLUORO(PYRIDINYL)METHYL]PHOSPHONATES

Authors

  • Oksana M. Shavrina Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02660, Ukraine
  • Petro P. Onys'ko Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02660, Ukraine
  • Yuliya V. Rassukana Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02660, Ukraine

DOI:

https://doi.org/10.1007/7468

Keywords:

aminophosphonic acids, (difluoromethyl)phosphonates, N-fluorobenzenesulfonimide, piperidines, pyridines, fluorination.

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.

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers