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Synthetic Applications of N-N Linked Heterocycles. Part 14. The Preparation of α-(4-Pyridyl)esters and α-(4-Pyridyl)nitriles by Regiospecific Attack of Ester and Nitrile Anions on Pyridinium Salts

DOI: 10.1039/P19810002476

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2476 - 2482 (1981)

Update date:2022-09-26

Topics:

Authors:

Sammes, Michael P.Sammes, Michael P.

Lee, Cheuk ManLee, Cheuk Man

Katritzky, Alan R.Katritzky, Alan R.

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Article abstract of DOI:10.1039/P19810002476

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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Product name:(3-Methyl-pyridin-4-yl)-phenyl-acetic acid ethyl ester

Cas No:79757-12-3

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