Síntese de Derivados do Glicerol Funcionalizados com Organocalcogênio utilizando PEG-400

Abstract

The organochalcogens, organic compounds that have in their structure calcogen atoms (S, Se, Te), are of great importance due to the presence in numerous reactions and to present diverse pharmacological properties. Because of this, a rapid and selective method for the synthesis of 4-thiomethyl-1,3-dioxolan-2-ones 3a-j was first developed using polyethylene glycol- 400 (PEG-400) as a green solvent promoted by alumina supported in potassium fluoride (KF/Al2O3) under microwave irradiation. In this first work it was possible to obtain 10 examples of the compounds 3a-j in moderate to excellent yields, which ranged from 40 to 88%. In addition, the method was explored to provide 3 examples of compound 4 in yields ranging from 65 to 97% (Scheme 1). Scheme 3 In a second work, following the interest in the synthesis of organochalcogens compounds, the reactivity of O-tosyl glycerol 1,2-carbonate 1 was explored, reacting three of the different electrophilic reactive sites present in this structure. The aim of this study was to obtain different methodologies for the preparation of 4-chalcogenylmethyl-1,3-dioxolan-2-ones 6, 1,3-bis (organylchalcogenyl)propan-2- ols symmetrical 7 and unsymmetrical 8 and 3-(arylchalcogenyl)propane-1,2-diols 9 (Scheme 2). The products of interest obtained in this work presented moderate to excellent yields, which varied from 40 to 96%.