Access to <sup>18</sup>F-labelled isoxazoles by ruthenium-promoted 1,3-dipolar cycloaddition of 4-[<sup>18</sup>F]fluoro-<i>N</i>-hydroxybenzimidoyl chloride with alkynes

  1. Roscales García, Silvia 1
  2. Kniess, Torsten 1
  1. 1 Institute of Radiopharmaceutical Cancer Research; Helmholtz-Zentrum Dresden-Rossendorf; Dresden Germany
Revista:
Journal of Labelled Compounds and Radiopharmaceuticals

ISSN: 1099-1344

Año de publicación: 2019

Volumen: 62

Número: 8

Páginas: 393-403

Tipo: Artículo

DOI: 10.1002/JLCR.3708 GOOGLE SCHOLAR lock_openAcceso abierto editor

Otras publicaciones en: Journal of Labelled Compounds and Radiopharmaceuticals

Resumen

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.

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