Electrogenerated cyanomethyl anion in organic synthesis. Synthesis of 1,3-oxazolidine-2,4-diones

Cyanomethyl and 3-aminocrotonitrile anions, generated by cathodic reduction of CH3CN-Et4NClO4 solution under galvanostatic control are used in combination with gaseous CO2, as an alternative carboxylating reagent for the synthesis of oxazolidine-2,4-diones starting from halo amides. The synthesis has been carried out under mild conditions, avoiding any addition of classical bases, catalysts or toxic and dangerous chemicals. Reaction yields were moderate to very good (43-90%).