Abstract
The reactions are reported of 4-(furan-3-ylcarbonyl)-1,5-diphenylpyrrolidine-2,3-dione with six classes of organophosphorus reagents: carboalkoxymethylene triphenylphosphoranes, triphenyl (phenylimino)-λ5-phosphane, trialkylphosphonoacetates, trialkylphosphites, tris (dialkylamino)phosphines, and Lawesson's reagent. Several of the products showed antitumour activity.
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