Quinuclidine and DABCO Enhance the Radiofluorination of 5‐Substituted 2‐Halopyridines Article Swipe
Gregory R. Naumiec
,
Lisheng Cai
,
Shuiyu Lu
,
Victor W. Pike
·
YOU?
·
· 2017
· Open Access
·
· DOI: https://doi.org/10.1002/ejoc.201700970
YOU?
·
· 2017
· Open Access
·
· DOI: https://doi.org/10.1002/ejoc.201700970
Positron emission tomography (PET) is an important molecular imaging technique for medical diagnosis, biomedical research and drug development. PET tracers for molecular imaging contain β + ‐emitting radionuclides, such as carbon‐11 ( t 1/2 = 20.4 min) or fluorine‐18 ( t 1/2 = 109.8 min). The [ 18 F]2‐fluoropyridyl moiety features in a few prominent PET radiotracers, not least because this moiety is usually resistant to unwanted radiodefluorination in vivo. Various methods have been developed for labeling these radiotracers from cyclotron‐produced no‐carrier‐added [ 18 F]fluoride ion, mainly based on substitution of a leaving group, such as halide (Cl or Br), or preferably a better leaving group, such as nitro or trimethylammonium. However, precursors with a good leaving group are sometimes more challenging or lengthy to prepare. Methods for enhancing the reactivity of more readily accessible 2‐halopyridyl precursors are therefore desirable, especially for early radiotracer screening programs that may require the quick labeling of several homologous radiotracer candidates. In this work, we explored a wide range of additives for beneficial effect on nucleophilic substitution by [ 18 F]fluoride ion in 5‐substituted 2‐halopyridines (halo = Cl or Br). The nucleophilic cyclic tertiary amines, quinuclidine and DABCO, proved effective for increasing yields to practically useful levels (> 15 %). Quinuclidine and DABCO likely promote radiofluorination through reversible formation of quaternary ammonium intermediates.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/ejoc.201700970
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/ejoc.201700970
- OA Status
- bronze
- Cited By
- 23
- References
- 43
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2736722163
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W2736722163Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1002/ejoc.201700970Digital Object Identifier
- Title
-
Quinuclidine and DABCO Enhance the Radiofluorination of 5‐Substituted 2‐HalopyridinesWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
-
2017Year of publication
- Publication date
-
2017-07-25Full publication date if available
- Authors
-
Gregory R. Naumiec, Lisheng Cai, Shuiyu Lu, Victor W. PikeList of authors in order
- Landing page
-
https://doi.org/10.1002/ejoc.201700970Publisher landing page
- PDF URL
-
https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/ejoc.201700970Direct link to full text PDF
- Open access
-
YesWhether a free full text is available
- OA status
-
bronzeOpen access status per OpenAlex
- OA URL
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/ejoc.201700970Direct OA link when available
- Concepts
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DABCO, Chemistry, Quinuclidine, Moiety, Nucleophilic substitution, Nucleophile, Combinatorial chemistry, Leaving group, Medicinal chemistry, Stereochemistry, Organic chemistry, Octane, CatalysisTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
23Total citation count in OpenAlex
- Citations by year (recent)
-
2024: 8, 2022: 1, 2021: 2, 2020: 4, 2019: 5Per-year citation counts (last 5 years)
- References (count)
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43Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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