Síntese de α-organiltio-hidróxicetonas empregando Sais de Bunte em meio básico

Abstract

This work addresses the study and development of a new protocol for the synthesis of α- organoylthiohydroxyketones prepared through thiolation reactions between Bunte Salts (sodium S-organoyl sulfothioates) and 1,3-dicarbonyl compounds in basic medium, using toluene as solvent at 110 °C under ambient atmosphere. Having found the ideal condition for promoting these molecules, the generality and scope of the protocol were tested by employing Bunte Salts containing electron donor and electron withdrawing substituents as well as symmetric and asymmetric 1,3-dicarbonyl compounds. Through this methodology, it was possible to obtain 13 examples of α-organoylthiohydroxyketones, 12 of them unpublished, with yields ranging from 11 to 91%, in relatively short reaction period (2 hours). The developed protocol stands out for the use of substrates that are stable to the environment and humidity, not presenting an unpleasant odor, as well as for being free of transition metals. Molecular docking studies are being carried out in order to evaluate the biological potential of the synthesized compounds.