Reactions of 4-Hydroxycoumarin with Alpha-Cyanocinnamates

Abstract

During attempts to prepare precursors for warfarin labeled with a protein tag, it was found that many of the reactions beginning with warfarin itself failed to give the desired products, but led, instead, to cyclized products. In an effort to overcome these difficulties, a potential warfarin-like compound was prepared by the reaction between alpha-cyanocinnamates and 4-hydroxycoumarin in pyridine. The reaction did not give the expected warfarin-like product, but another set of cyclized products. The purpose of this study was the synthesis of the alpha-cyanocinnamates and the products of their reactions with 4-hydroxycoumarin.