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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky St., Irkutsk, 664033, Russia

    N. A. Nedolya, O. A. Tarasova, O. G. Volostnykh, A. I. Albanov & B. A. Trofimov

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  1. N. A. Nedolya
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  2. O. A. Tarasova
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  3. O. G. Volostnykh
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  4. A. I. Albanov
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  5. B. A. Trofimov
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Correspondence to N. A. Nedolya.

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*Dedicated to M. G. Voronkov on his 90th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1718-1724, November, 2011.

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Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G. et al. Reactions of 2-aza-1,3,5-trienes with superbases: competition between formation of thiazoles and azepines. Chem Heterocycl Comp 47, 1430–1435 (2012). https://doi.org/10.1007/s10593-012-0930-5

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  • DOI: https://doi.org/10.1007/s10593-012-0930-5

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