Oxidative Cyclisation of 3-Oxopropanenitriles Mediated Manganese(III) Acetate with 2-Thienyl Substituted Alkenes

Authors: MEHMET YILMAZ, NEŞE UZUNALİOĞLU, MEHTAP YAKUT, A. TARIK PEKEL

Abstract: The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group by manganese(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 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-(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

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