Fast 62–92 % yield preparation of amino acid dithiocarbamates in green solvent at room temperature

Abstract

Dithiocarbamate and their derivatives are of importance in medicinal chemistry due to their biological activities, in agriculture as fungicides and in organic synthesis as versatile synthetic intermediates. Green solvents such as deep eutectic solvents and polyethylene glycol are new emerging alternatives to conventional harmful organic solvents. Here, we report the synthesis of amino acid–based dithiocarbamates by one-pot three-component reaction of the electrophilic reagent, carbon disulfide and α-amino acids in deep eutectic solvent and polyethylene glycol as a catalyst and reaction media. In situ preparation of dithiocarbamates by the reaction of different amino acids and carbon disulfide, followed by addition reaction with epoxides, alkyl halides and α, β-unsaturated enones at room temperature, gave the corresponding products in 62–92 % yield with a short reaction time without any tedious workup procedures. The deep eutectic solvents and polyethylene glycol were recycled without activity or yield decrease. Therefore, the synthesis of amino acid–based dithiocarbamates in green solvents is a promising alternative to previously used procedures.