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Abstract
Microwave irradiation and conventional thermal heating techniques for the condensation of 2-[methyl(4-methylphenyl)- methylene]butanedioic anhydride 1), 2-[methyl(4-chlorophenyl)-methylene]butanedioic anhydride (2), or 2-diphenylmethylene-butanedioic anhydride (3)with different N-substituted 4-amino-benzenesulfonamides give the corresponding N-(N’-substituted benzenesulfonamido)-3-carboxy-4-aryl-3-butenamide derivatives, N-(N’-substituted benzenesulfonamido)-3-arylethylidinepyrrolidine-2,5-dione derivatives and N-(N’-substituted benzenesulfonamido)-3-diphenylmethylenepyrrolidine-2,5-dione derivatives (4-49).
The results obtained show that microwave irradiation technique furnishes the formation of the products in excellent yield, in shorter time, and more regiospecific than the conventional thermal heating one.
Some synthesized compounds show antimicrobial biological activity depending on the substituents.
The benzenesulfonamido group results in low reactivity toward condensation whereas it shows high biological activity.
The structural formulas of the products were confirmed by their spectral analysis; 1HNMR, MS and IR.