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

Koki Maruno; Kenshiro Hada; Yuji Sumii; Osamu Nagata; Norio Shibata

doi:10.1021/acs.orglett.2c01046

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

Org Lett. 2022 Jun 3;24(21):3755-3759. doi: 10.1021/acs.orglett.2c01046. Epub 2022 Apr 27.

Authors

Koki Maruno¹, Kenshiro Hada¹, Yuji Sumii¹, Osamu Nagata², Norio Shibata^{1

3}

Affiliations

¹ Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
² Pharmaceutical Division, Ube Industries, Ltd., Seavans North Bldg., 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan.
³ Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

PMID: 35475347
DOI: 10.1021/acs.orglett.2c01046

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes*
Cycloaddition Reaction
Pyridines*

Substances

Alkynes
Pyridines