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 |
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| Authors: | N A Nedolya O A Tarasova O G Volostnykh A I Albanov |
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| Institution: | (1) A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia |
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| 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.
Dedicated to Academician B. A. Trofimov of the Russian Academy of Sciences on his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1380–1383, September, 2008. |
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| Keywords: | azatrienes 3H-azepines deprotonation isothiocyanates propargylthiophene electrocyclization |
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