Síntese de benzamidas organocalcogeno-propargílicas mediada por sais de cobre

Abstract

The present work describes an alternative method for the synthesis of organochalcogen- propargylic benzamides through cross-coupling reactions of propargylic amides promoted by copper iodide and diorganyl dichalcogenides. This methodology provided 9 examples of organoselanyl-propargylic benzamide derivatives in yields ranging from 45 to 87%. The cross-coupling reactions carried out for 24 to 48 hours under room atmosphere at room temperature by employing catalytic amounts of CuI. Both benzamides and organocalcogens (containing atoms S, Se and Te) are of great pharmaceutical interest because of the biological importance of these compounds. Benzamides have antiviral, antimicrobial and antiparasitic properties, among other pharmacological effects. It was verified through the theoretical review, the large applicability of copper salts catalysts, because its use is environmentally favorable and relatively low cost. The reactions proved to be efficient using both diorganyl diselenides and propargylic amides bearing neutral, donor and electron-withdrawing groups.