Monocyanomethylated thiacalix[4]arenes: synthesis and lower rim modification

Abstract

The selective monocyanomethylation of p-R-thiacalix [4]arenes (R = H, tert-Bu) with chloroacetonitrile in the presence of Na 2 CO 3 in DMF is described.Monocyanomethylated p-tertbutylthiacalix[4]arene has been synthetically exploited in the Ritter reaction with 1-adamantanol for the transformation to the corresponding amide.A thiacalix[4]arene having mixed amide and ester functionalities at the lower rim was synthesized by alkylation of 25-N-(1adamantyl)carbamoylmethoxy-p-tert-butylthiacalix[4]arene with ethyl bromoacetate.