Title of article :
Oxidative Cyclisation of 3-Oxopropanenitriles Mediated Manganese(III) Acetate with 2-Thienyl Substituted Alkenes
Author/Authors :
YILMAZ, Mehmet Kocaeli University - Faculty of Arts and Sciences - Department of Chemistry, TURKEY , UZUNALIOGLU, Nese Ankara Üniversitesi - Faculty of Science - Department of Chemistry, TURKEY , YAKUT, Mehtap Ankara Üniversitesi - Faculty of Science - Department of Chemistry, TURKEY , PEKEL, A. Tarık Department of Chemistry - Faculty of Science - Ankara University, TURKEY
Abstract :
The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group bymanganese(III) 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 oxidativecyclisation of these 3-oxopropanenitriles with 2-[(E)-1-methyl-2-phenylvinyl]thiophene 2b in good yields(54%-68%). In addition, the reactions of 2-(1-phenylvinyl)thiophene 2c with various 3- oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.
Keywords :
Manganese(III) acetate , oxidative cyclisation , 4 , 5 , dihydrofuran , 3 , carbonitrile , 3 , oxopropanenitrile , conjugated alkene , radical addition
Journal title :
Turkish Journal of Chemistry
Journal title :
Turkish Journal of Chemistry
