Synthesis of 1-(1-Arylvinyl)pyridin-2(1 <i>H</i> )-ones from Ketones and 2-Fluoropyridine

Синтез 1-(1-арилвинил)pyridin-2(1H)-онов из кетонов и 2-фторпиридина
Akio Kamimura, Takuji Kawamoto, Shunya Ikeda
2021-09-21

1-(1-Arylvinyl)pyridin-2(1H)-ones2-fluoropyridinemechanistic studytrifluoromethanesulfonic anhydridevinyl-substituted pyridones
-vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by a base treatment. Various ketones with electron-donating or electron-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.
1
A method to synthesize 1-(1-arylvinyl)pyridin-2(1H)-ones from ketones and 2-fluoropyridine using trifluoromethanesulfonic anhydride followed by base treatment.
2
Preliminary mechanistic study suggests vinyl triflates and vinyl cations are unlikely to be major intermediates in this transformation.
3
The reaction tolerates various ketones bearing either electron-donating or electron-withdrawing groups on the benzene ring.

Synthesis reaction producing 1-(1-arylvinyl)pyridin-2(1H)-ones from ketones and 2-fluoropyridine using trifluoromethanesulfonic anhydride and base

Scope, substituent tolerance, and preliminary mechanism of the transformation including evaluation of possible intermediates (vinyl triflates and vinyl cations) for forming 1-(1-arylvinyl)pyridin-2(1H)-ones

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2021-09-21
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Authors
Akio Kamimura
Takuji Kawamoto
Shunya Ikeda
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