Ultrasound-promoted solvent-free aza-Michael addition of p-toluenesulfonamide to fumaric esters by potassium carbonate: Synthesis of p-toluenesulfonamide derivatives

An efficient, mild, inexpensive and eco-friendly protocol for the synthesis of p-toluenesulfonamide derivatives by aza-Michael addition reaction of p-toluenesulfonamide to fumaric esters using potassium carbonate under ultrasound irradiation was developed. This method is simple, convenient and the desired compounds are produced in good to excellent yield. The bulkiness of alkoxy group (–OR) of fumaric esters did not affect significantly on the yields and reaction times. This reaction worked well on linear and nonlinear alkyl fumarates. The reaction, surprisingly, was not successful on methyl fumarate. In this case methyl fumarate has been hydrolyzed to fumaric acid under reaction conditions.

► Ultrasound promoted aza-Michael reaction of p-toluenesulfonamide and fumaric esters. ► The bulkiness of alkoxy group did not affect on the yields and reaction times. ► The reaction worked well on linear and nonlinear alkyl fumarates. ► Methyl fumarate has been hydrolyzed to fumaric acid under reaction conditions.