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Synthesis of 1-(1-Arylvinyl)pyridin-2(1H)-ones from Ketones and 2-Fluoropyridine

preprint
submitted on 05.03.2021, 00:51 and posted on 08.03.2021, 05:23 by Takuji Kawamoto, shunya ikeda, Akio Kamimura
Pyridone skeletons are found in numerous biologically active molecules and pharmaceuticals. 1-(1-Arylvinyl)pyridin-2(1H)-ones are synthetic intermediates derived from the enamide moiety, and only few examples of the synthesis of 1-(1-arylvinyl)-2-pyridones have been reported. In this work, a simple and efficient procedure for the synthesis of N-vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by base treatment is described. Various ketones with electron-donating or -withdrawing groups at the benzene rings can be used in this reaction. A preliminary mechanistic study indicates that it is not very likely that both vinyl triflates and vinyl cations play major roles as intermediates in this transformation. The thus obtained pyridones can be subsequently transformed via C–H arylation and radical alkylation reactions.

Funding

a JSPS Grant-in-Aid for Young Scientists (B) (18K14222)

the Yamagin Regional Enterprise Support Foundation

the Tobe Maiki Scholarship Foundation

History

Email Address of Submitting Author

tak102@yamaguchi-u.ac.jp

Institution

Yamaguchi University

Country

Japan

ORCID For Submitting Author

0000-0002-1845-4700

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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