NEW APPROACH TO THE FORMATION OF AZEPINE RING: SYNTHESIS OF 2-METHYL-6-(5-METHYL-2-THIENYL)-3H-AZEPINE FROM 2-METHYL-5-PROPARGYLTHIOPHENE AND ISOTHIOCYANATE

Authors

  • Н. А. Недоля A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • О. А. Тарасова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • О. Г. Волостных A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • А. И. Албанов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033

DOI:

https://doi.org/10.1007/7202

Keywords:

azatrienes, 3H-azepines, deprotonation, isothiocyanates, propargylthiophene, electrocyclization

Abstract

The first representative of thienyl-substituted 3H-azepines has been synthesized starting from dilithiated 2-methyl-5-propargylthiophene and isopropyl isothiocyanate. It was shown that N-(1-methylethylidene)-2-(5-methyl-2-thienyl)-1-(methylthio)-1,3-butadiene-1-amine (2-aza-1,3,5-triene) formed as a result of this reaction is readily converted into 2-methyl-6-(5-methyl-2-thienyl)-3H-azepine under the action of super bases.

How to Cite
Nedolya, N. A.; Tarasova, O. A.; Volostnykh, O. G.; Albanov, A. I.  Chem. Heterocycl. Compd. 2008, 44, 1113. [Khim. Geterotsikl. Soedin. 2008, 1380.]

For this article in the English edition see DOI 10.1007/s10593-008-0161-y


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Published

2022-11-24

Issue

No. 9 (2008)

Section

Original Papers