Tricyanovinylation of 2-aryl-1-vinylpyrroles: solvent- and substituent controlled chemo- and regioselectivity |
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Authors: | Boris A Trofimov Lyubov' N Sobenina Vladislav N Drichkov Igor' A Ushakov Al'bina I Mikhaleva |
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Institution: | A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia |
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Abstract: | 2-Aryl-1-vinylpyrroles in acetone, THF and benzene react with tetracyanoethene chemo- and regiospecifically across the vinyl group to give 3-(2-arylpyrrol-1-yl)-1,1,2,2-cyclobutanetetracarbonitriles in 88-94% yield. The latter, upon recrystallization from EtOH, eliminates HCN and entirely rearranges to afford stereospecifically trans-(3E)-4-(2-arylpyrrol-1-yl)-1,3-butadiene-1,1,2-tricarbonitriles. In DMSO, along with the above 2+2]-cycloaddition, tricyanovinylation of the pyrrole ring occurs to form the corresponding 3- and 5-tricyanovinylpyrroles, the product ratio being dependent on the substituents in the pyrrole ring and the reaction conditions. |
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