Synthesis of Pyridine–SF4–Isoxazolines Using the Functionality of trans-Tetrafluoro‑λ6‑sulfanyl Rodlike Linkers

The tetrafluoro-λ6-sulfanyl (SF4) moiety has been relatively undeveloped since its discovery in the 1970s. In this study, we synthesized pyridine–SF4–isoxazolines, in which the two heterocycles are connected by a rodlike trans-SF4 linker, via the regioselective 1,3-dipolar cycloaddition of pyridine–...

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Bibliographic Details
Published in:Organic letters 2022-06, Vol.24 (21), p.3755-3759
Main Authors: Maruno, Koki, Hada, Kenshiro, Sumii, Yuji, Nagata, Osamu, Shibata, Norio
Format: Article
Language:English
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Summary:The tetrafluoro-λ6-sulfanyl (SF4) moiety has been relatively undeveloped since its discovery in the 1970s. In this study, we synthesized pyridine–SF4–isoxazolines, in which the two heterocycles are connected by a rodlike trans-SF4 linker, via the regioselective 1,3-dipolar cycloaddition of pyridine–SF4–alkynes and nitrones in the presence of triethylamine. SF4 linkers are a viable alternative to para-substituted benzenes, alkynes, and bicyclo[1.1.1]­pentyl derivatives in drug design, and pyridine–SF4–isoxazolines have potential applications in drug development.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01046