We describe here a simple method for the synthesis of glycerol derivatives containing an organochalcogen unit (Se, Te and S) using NaBH4 and PEG-400 as a solvent. The new methodology was used to synthesize a range of new organochalcogen compounds in good yields. Furthermore, four of synthesized compounds were evaluated for their antioxidant activity using different assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, nitric oxide (NO) and hydroxyl radical (OH) scavenging, ferric ion reducing antioxidant power (FRAP), ferrous ion chelating, superoxide dismutase-like activity and inhibition of linoleic acid lipid peroxidation. The new organotellurium 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j showed antioxidant activity and was more effective in inhibition of induced lipid peroxidation compared to solketal 4. Selenium and sulfur analogs 3a and 3m and solketal 4 did not present antioxidant effect. These findings suggest that 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.

No abstract

We describe a selective method for synthesis of 4‐chalcogenylmethyl‐1,3‐dioxolan‐2‐ones and 1,3‐bis(organylchalcogenyl)propan‐2‐ols in a short reaction time through stoichiometric control. The use of 3‐O‐tosyl glycerol 1,2‐carbonate and a set of aryl and alkyl diorganyl dichalcogenides afforded the desired products in good to excellent yields. We also describe a synthetic application to 4‐chalcogenylmethyl‐1,3‐dioxolan‐2‐ones by base promoted the synthesis of 3‐(arylchalcogenyl)propane‐1,2‐diols in excellent yields.

No abstract