REACTIONS OF 2-AZA-1,3,5-TRIENES WITH SUPERBASES: COMPETITION BETWEEN FORMATION OF THIAZOLES AND AZEPINES

Authors

  • Н. А. Недоля A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • О. А. Тарасова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • О. Г. Волостных A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • А. И. Албанов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Б. А. Трофимов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1353

Keywords:

azatrienes, 3H-azepines, dihydrothiazoles, isothiocyanates, methoxyallene, deprotonation, heterocyclization, superbases

Abstract

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.

Authors: N. A. Nedolya, O. A. Tarasova, O. G. Volostnykh, A. I. Albanov, and B. A. Trofimov.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (11), pp 1430-1435

http://link.springer.com/article/10.1007/s10593-012-0930-5

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Published

2013-12-12

Issue

No. 11 (2011)

Section

Original Papers