Journal of the Chemical Society. Perkin transactions I p. 2476 - 2482 (1981)
Update date:2022-09-26
Topics:
Sammes, Michael P.
Lee, Cheuk Man
Katritzky, Alan R.
Reactions between N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium tetrafluoroborate (1) and lithio-derivatives of esters and nitriles give only low yields of 1,4-dihydro-adducts (3) and (7) due apparently to competing proton abstraction from the pyridone methyl groups.This limitation with salt (1) appears only with C-H acids of pKa > 20.Decomposition of the adducts under free-radical conditions yields α-(4-pyridyl)-esters (4) and -nitriles (8) essentially quantitatively.The same pyridyl-esters and -nitriles may be prepared conveniently in good overall yields by the reaction between the appropriate lithium salts and N-triphenylmethylpyridinium salts.The scope and limitations of the method are discucced. 2-Methyl-N-triphenylmethylpyridinium tetrafluoroborate is reported for the first time.
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Doi:10.1246/cl.1981.615
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