Synthesis of 6-substituted 2-phenacylpyridines from 2-(phenylethynyl)pyridine via isoxazolo[2,3-a]pyridinium salt?
Organic & Biomolecular Chemistry Pub Date: 2016-10-24 DOI: 10.1039/C6OB01942K
Abstract
When 2-(phenylethynyl)pyridine was oxidized, the formed N-oxide immediately cyclized at the ethynyl group to form isoxazolo[2,3-a]pyridinium salt. This salt underwent Reissert–Henze-type reactions with alcohol in the presence of a base to afford 6-substituted 2-phenacylpyridines, which are not easily synthesized through alternative procedures. When acetonitrile was used as a solvent, an amide functional group was introduced into the phenacylpyridine framework. Moreover, a hetero-atom at the 6-position facilitated the oxidation of the phenacyl group to afford α-diketones upon simple exposure of the reaction mixture to air.
![Graphical abstract: Synthesis of 6-substituted 2-phenacylpyridines from 2-(phenylethynyl)pyridine via isoxazolo[2,3-a]pyridinium salt](http://scimg.chem960.com/usr/1/C6OB01942K.jpg)
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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