Oxidative cyclisation of 3-oxopropanenitriles mediated manganese(III) acetate with 2-thienyl substituted Alkenes


YILMAZ M. , UZUNALIOGLU N., YAKUT M., PEKEL A. T.

TURKISH JOURNAL OF CHEMISTRY, cilt.32, ss.411-422, 2008 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 32 Konu: 4
  • Basım Tarihi: 2008
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.411-422

Özet

The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group by manganese(111) acetate was studied. Treatment of 3-oxopropanenitriles 1a-d with 2-[(E)-2-phenylvinyl] thiophene 2a gave 4-phenyl-5-(2-thienyl)-4,5-dihydrofuran-3-carbonitriles 3a-d in moderate yields (52%60%). 5-(2-thienyl) substituted 4,5-dihydrofuran-3-carbonitriles 3e-i were obtained by the oxidative cyclisation of these 3-oxopropanenitriles with 2-[(E)-1-methyl-2-phenylvinyl]thiophene 2b in good yields (54%-68%). In addition, the reactions of 2-(I-phenylvinyl)thiophene 2c with various 3-oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.