Pd(ii)-Catalyzed alkyne annulation through allylic isomerization: synthesis of spiro-cyclopentadiene pyrazolones

Abstract

The Pd(II)-catalyzed activation of Csp²–H bond and double alkyne annulation which proceeds via allylic isomerization is reported for the first time. This reaction of antipyrines with alkynes provides an efficient synthetic route for the biologically important spiro-cyclopentadiene pyrazolones. In the presence of Lawesson's reagent, this Pd(II)-catalyzed annulation reaction affords another spiro-cyclopentadiene pyrazolone which displays very good fluorescence properties.