Dehydrative formation and biological evaluation of allylic sulfonamides from allylic alcohols using recyclable silica-supported acid catalysts

Abstract

A reusable transition-metal-free catalytic system has been developed to facilitate the dehydrative sulfonamidation of primary and secondary allylic alcohols under mild reaction conditions. The method employs p-toluenesulfonic acid as an immobilized Brønsted acid on a silica gel solid-support, and the catalytic system has been shown to be recyclable without significant loss of activity for 3–5 uses. A wide range of sulfonamide and allylic alcohol substrates are tolerated in this transformation, and products have been isolated from reactions employing known pharmaceuticals such as celecoxib and methocarbamol as nucleophilic substrates. The antibacterial, antifungal, and cytotoxic properties of the isolated products was investigated along with their activity as metabolic inhibitors of ATP production.