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Synthetic Applications of N-N Linked Heterocycles. Part 12. The Preparation of 4-Alkylthio- and 4-Arylthio-pyridines by Regiospecific Attack of Thioalkoxide Ions on N-(4-Oxopyridin-1-yl)pyridinium Salts

DOI: 10.1039/P19810001585

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1585 - 1590 (1981)

Update date:2022-08-03

Topics:

Authors:

Sammes, Michael P.Sammes, Michael P.

Leung, Christopher W. F.Leung, Christopher W. F.

Mak, Chi KeungMak, Chi Keung

Katritzky, Alan R.Katritzky, Alan R.

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Article abstract of DOI:10.1039/P19810001585

Thiolate ions add regiospecifically to N-(4-oxopyridin-1-yl)pyridinium salts (2)-(7) to give in good to excellent yields only the 1,4-dihydropyridine adducts (8)-(13), regardless of whether or not the pyridone moiety carries substituents for sterically shielding the 2- and 6-positions of the pyridinium ring.The addition is believed to be thermodynamically controlled.Decomposition of the dihydro-adducts under free-radical conditions, or by pyrolysis, gives good yields of pyridin-4-yl thioethers (14) and (16) though the reaction failed with the 2-methyl adducts (9).An improved synthesis of 6-methyl-4-oxopyran-2-carboxylic acid is also described.

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Product name:4'-(4-Chloro-phenylsulfanyl)-2,6,3'-trimethyl-4'H-[1,1']bipyridinyl-4-one

Cas No:78526-38-2

78526-38-2

R&D Labs maybe for 78526-38-2

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