Synthesis of Pyridine–SF<sub>4</sub>–Isoxazolines Using the Functionality of <i>trans</i>-Tetrafluoro-λ<sup>6</sup>-sulfanyl Rodlike Linkers
Koki Maruno, Kenshiro Hada, Yuji Sumii, Osamu Nagata, Norio Shibata
Abstract
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.
Topics & Concepts
PyridineChemistryMoietyRegioselectivitySulfanylCycloaddition1,3-Dipolar cycloadditionLinkerIndolizineStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisOperating systemComputer scienceFluorine in Organic ChemistryClick Chemistry and ApplicationsSynthesis and Catalytic Reactions