Cycloaddition of nitrileimines to resin-bound enamines: a solid phase synthesis of 1,4-diarylpyrazoles

Abstract

The 1,3-dipolar cycloaddition reaction between nitrile imines and resin-bound enamines gives resin-bound pyrazoline intermediates. The piperazine resin functions as a traceless linker and allows these intermediates to be cleaved directly from the resin under mild acid conditions to afford 1,4-diarylpyrazoles. Alternatively they may be chemically modified on the resin prior to elimination from the polymer. The cycloaddition–elimination sequence is regiospecific for the 3,4-disubstituted pyrazole isomer and the products are obtained in good to high yield and in high purity.