ArticleChemical communications (Cambridge, England)2016
Synthesis of meta-substituted [(18)F]3-fluoro-4-aminopyridine via direct radiofluorination of pyridine N-oxides.
Article in Chemical communications (Cambridge, England), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 30 citations in OpenAlex.
- Article
- Synthesis of KBioorganic & medicinal chemistry letters · 2024Article
- Chemical and biophysical characterization of novel potassium channel blocker 3-fluoro-5-methylpyridin-4-amine.Scientific reports · 2024Article
- SThe Journal of organic chemistry · 2021Article
- Evaluation of the potassium channel tracer [Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism · 2021Article
- Radiochemical Synthesis and Evaluation in Non-Human Primates of 3-[ACS chemical neuroscience · 2021Article
- Structure-activity relationship studies of four novel 4-aminopyridine KScientific reports · 2020Article
- An efficient new method for the synthesis of 3-[Journal of labelled compounds & radiopharmaceuticals · 2018Article
- Development of a PET radioligand for potassium channels to image CNS demyelination.Scientific reports · 2018Article
- Automated Radiochemical Synthesis of [18F]3F4AP: A Novel PET Tracer for Imaging Demyelinating Diseases.Journal of visualized experiments : JoVE · 2017Article
- Detecting Demyelination by PET: The Lesion as Imaging Target.Molecular imagingArticle
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4 authors at 2 institutions in 1 country.
Funding
Abstract
Due to their electron-rich aromatic structure, nucleophilic (radio)fluorination of pyridines is challenging, especially at the meta position. In this paper, we describe the first example of direct fluorination of a pyridine N-oxide to produce a meta fluorinated pyridine. Specifically, fluorination of 3-bromo-4-nitropyridine N-oxide produced in several minutes 3-fluoro-4-nitropyridine N-oxide in moderate yield at room temperature. This intermediate compound was later converted to 3-fluoro-4-aminopyridine easily by catalytic hydrogenation. Furthermore, this approach was successfully applied for labeling with fluorine-18. The use of pyridine N-oxides for the preparation of fluoropyridines is unprecedented in the chemical literature and has the potential to offer a new way for the synthesis of these important structures in pharmaceuticals and radiopharmaceuticals.
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