Unexpected elimination of methanol from 6-(alkylsulfanyl)-5-methoxy-2,3-dihydropyridines using t-BuOK-DMSO: an access to 2-alkyl-6-(alkyl-sulfanyl)pyridines
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Novel data has been obtained regarding the synthetic potential of our discovery of the reaction of allene carbanions with aliphatic isothiothiocyanates which can lead to a novel class of pyrroles and highly stable 2,3-dihydropyridines [1, 2, 3]. In particular, it was shown that the 6-(alkylsulfanyl)-5-methoxy-2,3-dihydro-pyridines obtained in this way readily lose methanol using t-BuOK in DMSO to form the previously unknown and practically unavailable 2-alkyl-6-(alkylsulfanyl)pyridines.
Keywords2-alkyl-6-(alkylsulfanyl)pyridines t-BuOK-DMSO 2,3-dihydropyridines isothiocyanate methanol methoxyallene elimination synthesis
This work was carried out with financial support of the Russian Fund for Basic Research (project 09-03-00890a).
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