Bunte salts-promoted transition-metal-free sulfenylation of 1,3-diketones: Design, synthesis and in silico evaluation of 3-(organylthio)-4-hydroxyalken-2-ones

Organosulfur compounds are very useful tools in organic synthesis, being efficiently employed as synthetic precursors and intermediates in several chemical processes. In this context, sodium S-organyl sulfurothioates, usually referred to as Bunte salts, have recently emerged as an alternative and powerful tools for the synthesis of a wide range of organosulfur derivatives. Herein, we reported the use of Bunte salts as versatile, odorless, air stable, and easy-to-handle organosulfur sources for the sulfenylation of 1,3-diketones, affording 3-(organylthio)-4-hydroxyalken-2-ones in good yields under basic and transition-metal-free conditions. The reaction proceeds smoothly under ambient atmosphere and is tolerant to the presence of electron-donating and withdrawing groups bonded to the aromatic rings of the Bunte salts, yielding the expected products after only 2 h. In addition, due to the well-known pharmacological properties of sulfur-containing organic substances and their presence in variety of drugs used for the treatment of several diseases, the synthesized compounds were submitted to molecular docking analysis. These studies demonstrated their potential to interact with serotonergic system targets and suggest they could be useful in the development of new therapeutic strategies for different neurological diseases.