Journal of the Chemical Society. Perkin transactions I p. 1585 - 1590 (1981)
Update date:2022-08-03
Topics:
Sammes, Michael P.
Leung, Christopher W. F.
Mak, Chi Keung
Katritzky, Alan R.
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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Doi:10.1016/S0040-4039(01)90273-4
(1981)Doi:10.1021/jo0496805
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(2018)Doi:10.1002/hlca.19810640309
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