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Mild synthesis of 2,3,5,6-tetrafluoropyridine ethers and their reactivity toward imidazole and pyrazole.
- Source :
-
Journal of Fluorine Chemistry . May2024, Vol. 276, pN.PAG-N.PAG. 1p. - Publication Year :
- 2024
-
Abstract
- • Nucleophilic aromatic substitution (SNAr) of pentafluoropyridine with aliphatic alcohols and phenols afforded a series of six 4-substituted 2,3,5,6-tetrafluoropyridine (TFP) hetero ethers. • 4-substituted TFP hetero ethers served as intermediates for the preparation of terepyridine scaffolds 3,5-difluoro-2,6-bis(pyrazolyl)pyridine and 4-(hexyloxy)−2,3,5,6-tetra(1H -pyrazol-1-yl)pyridine. • The highly organic soluble, low vapor pressure TFP hetero ethers should garner interest for weakly binding to heterogeneous surfaces and influence bulk properties by nature of the aliphatic/aromatic substitution. • 3,5-Difluoro-2,6-bis(pyrazolyl)pyridine and 4-(hexyloxy)−2,3,5,6-tetra(1H -pyrazol-1-yl)pyridine compounds could serve as strong metal binding as ligands or scaffolds within larger macromolecular systems. A series of six, 4-substituted 2,3,5,6-tetrafluoropyridine (TFP) hetero ethers have been synthesized via regio-selective, nucleophilic aromatic substitution (SNAr) of pentafluoropyridine with aliphatic alcohols and phenols. Furthermore, the hexyloxy modified TFP substrate also served as a synthetic intermediate for the preparation of 3,5-difluoro-4-(hexyloxy)-2,6-di(1H -imidazol-1-yl)pyridine, as well as 4-(hexyloxy)-2,3,5,6-tetra(1H -pyrazol-1-yl)pyridine, which offers a terpyridine scaffold. This work outlines their synthetic methodology in addition to detailing the TFP intermediates' unexpected reactivity with imidazole and pyrazole nucleophiles [Display omitted] [ABSTRACT FROM AUTHOR]
- Subjects :
- *ETHER synthesis
*PYRAZOLES
*VAPOR pressure
*ALIPHATIC alcohols
*PYRIDINE
*ETHERS
Subjects
Details
- Language :
- English
- ISSN :
- 00221139
- Volume :
- 276
- Database :
- Academic Search Index
- Journal :
- Journal of Fluorine Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 177601263
- Full Text :
- https://doi.org/10.1016/j.jfluchem.2024.110280