Tetrahedron

The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2 (5H)-ones

JT Gupton, N Telang, EJ Banner, EJ Kluball, KE Hall…

Index: Gupton, John T.; Telang, Nakul; Banner, Edith J.; Kluball, Emily J.; Hall, Kayleigh E.; Finzel, Kara L.; Jia, Xin; Bates, Spencer R.; Welden, R. Scott; Giglio, Benjamin C.; Eaton, James E.; Barelli, Peter J.; Firich, Lauren T.; Stafford, John A.; Coppock, Matthew B.; Worrall, Eric F.; Kanters, Rene P.F.; Keertikar, Kerry; Osterman, Rebecca Tetrahedron, 2010 , vol. 66, # 47 p. 9113 - 9122

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Citation Number: 9

Abstract

Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2 (5H)-ones from (Z)-3- aryl-3-haloenoic acids are described. The successful strategy relies on the preparation of (Z)- 3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3- haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl- 5H-furan-2-ones. The furanones were subsequently treated with primary amines and ...