Manganese(III) acetate based oxidative cyclizations of 3-oxopropanenitriles with conjugated alkenes and synthesis of 4,5-dihydrofuran-3-carbonitriles containing heterocycles


Yilmaz M. , UZUNALIOGLU N., PEKEL A. T.

TETRAHEDRON, cilt.61, ss.8860-8867, 2005 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 61 Konu: 37
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.07.019
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayısı: ss.8860-8867

Özet

,5-Dihydrofuran-3-carbonitriles 3a-i were obtained through oxidative cyclizations of 3-oxo-3-phenylpropanenitrile 1a, 3-oxo3-thien-2-ylpropanenitrile 1b, 3-(2-furyl)-3-oxopropanenitirle 1c, 3-(1-benzofuran-2-yl)-3-oxopropanenitrile 1d, and 4,4-dimethyl-3oxopropanenitrile 1e mediated manganese(III) acetate with 1,1-diphenyl-l-butene 2a and 1,2-diphenyl-1-pentene 2b. The treatments of these 3-oxopropanenitriles with 2-thienyl substituted alkenes such as 2-[(E)-2-phenylvinyl]thiophene 2c, 2-[(E)-1-methyl-2-phenylvinyl]thiophene 2d, and 2-(1-phenylvinyl)thiophene 2e formed 5 - (2-thienyl)-4,5 -dihydrofuran-3 -carbonitriles 3j-r in good yields (45-93%). As a result, 2-thienyl substituted alkenes formed products in higher yields than phenyl substituted derivatives. (c) 2005 Elsevier Ltd. All rights reserved.