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Access to 18F‐labelled isoxazoles by ruthenium‐promoted 1,3‐dipolar cycloaddition of 4‐[18F]fluoro‐N hydroxybenzimidoyl chloride with alkynes Roscales García, Silvia Kniess, Torsten 547 1,3‐dipolar cycloaddition 18F‐labelled isoxazoles alkynes Cp*RuCl(cod) Química orgánica (Química) 2306 Química Orgánica 4‐[18F]Fluoro‐N‐hydroxybenzimidoyl chloride (18FBIC), an 18F‐labelled aromatic nitrile oxide, was developed as building block for Ru‐promoted 1,3 dipolar cycloaddition with alkynes. 18FBIC is obtained in a one‐pot synthesis in up to 84% radiochemical yield (RCY) starting from [18F]fluoride with 4‐[18F]fluorobenzaldehyde (18FBA) and 4-[18F]fluorobenzaldehyde oxime (18FBAO) as intermediates, by reaction of 18FBAO with N‐chlorosuccinimide (NCS). 18FBIC was found to be a suitable and stable synthon to give access to 18F‐labelled 3,4‐diarylsubstituted isoxazoles by [Cp*RuCl(cod)]‐catalysed 1,3‐dipolar cycloaddition with various alkynes. So the radiosynthesis of a fluorine‐18–labelled COX‐2 inhibitor [18F]1b, a close derivative of valdecoxib, was performed with 18FBIC and 1‐ethynyl‐4‐(methylsulfonyl)benzene, providing [18F]1b in up to 40% RCY after purification in 85 minutes. The application of 18FBIC as a building block in the synthesis of 18F‐labelled heterocycles will generally extend the portfolio of available PET radiotracers. Fundación Ramón Areces Depto. de Química Orgánica Instituto Pluridisciplinar (IP) TRUE pub 2025-11-25T09:02:08Z 2025-11-25T09:02:08Z 2019 journal article VoR https://hdl.handle.net/20.500.14352/126453 XXXX-XXXX 10.1002/jlcr.3708 eng Roscales S, Kniess T. Access to18 F ‐labelled isoxazoles by ruthenium‐promoted 1,3‐dipolar cycloaddition of 4‐[18 F ]fluoro‐ N ‐hydroxybenzimidoyl chloride with alkynes. Labelled Comp Radiopharmac [Internet]. 30 de junio de 2019 [citado 25 de noviembre de 2025];62(8):393-403. Disponible en: https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/jlcr.3708 metadata only access application/pdf