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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 12, pp 1536–1538 | Cite as

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

  • N. A. Nedolya
  • O. A. Tarasova
  • A. I. Albanov
  • B. A. Trofimov
Article

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.

Thus the 5-methoxy-2-methyl-6-(methylsulfanyl)-2,3-dihydropyridine ( 1) (obtained by α-lithiation of methoxyallene and ethyl isothiocyanate in a single preparative stage 1) is readily converted by t-BuOK–DMSO at room temperature to the previously unknown 2-methyl-6-(methylsulfanyl)pyridine ( 3) in 83% yield (see Scheme below). The reaction occurs as a mild exotherm.

Keywords

2-alkyl-6-(alkylsulfanyl)pyridines t-BuOK-DMSO 2,3-dihydropyridines isothiocyanate methanol methoxyallene elimination synthesis 

Notes

This work was carried out with financial support of the Russian Fund for Basic Research (project 09-03-00890a).

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • N. A. Nedolya
    • 1
  • O. A. Tarasova
    • 1
  • A. I. Albanov
    • 1
  • B. A. Trofimov
    • 1
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of SciencesIrkutskRussia

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