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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 11, pp 1430–1435 | Cite as

Reactions of 2-aza-1,3,5-trienes with superbases: competition between formation of thiazoles and azepines

  • N. A. NedolyaEmail author
  • O. A. Tarasova
  • O. G. Volostnykh
  • A. I. Albanov
  • B. A. Trofimov
Article

For the case of 1-(allylsulfanyl)-2-methoxy-N-(1-methylethylidene)buta-1,3-dien-1-amine, obtained from α-lithiated methoxyallene, isopropyl isothiocyanate, and allyl bromide, it was shown that 5-ethylidene-2-(1-methoxyprop-2-enyl)-4,4-dimethyl-4,5-dihydro-1,3-thiazole and 6-methoxy-2-methyl-3H-azepine are formed competitively upon the action of the t-BuOK–THF–DMSO system.

Keywords

azatrienes 3H-azepines dihydrothiazoles isothiocyanates methoxyallene deprotonation heterocyclization superbases 

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • N. A. Nedolya
    • 1
    Email author
  • O. A. Tarasova
    • 1
  • O. G. Volostnykh
    • 1
  • A. I. Albanov
    • 1
  • B. A. Trofimov
    • 1
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

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