Electrosynthesis of hydroquinonethioethers using electrochemical oxidation of hydroquinone in the presence of thiouracil derivatives

Electrochemical oxidation of hydroquinone (1a) has been studied in the presence of 6-methyl-2-thiouracil (3a) and 6-propyl-2-thiouracil (3b) as nucleophiles in a DMF/buffer mixture, using cyclic voltammetry and controlled-potential coulometry. The results indicated that the p-quinone (2a) derived from 1a participates in a 1,4-Michael addition reaction with the thiouracil derivatives (3a–b) to form the corresponding hydroquinonethioether derivatives (6a–6b). The electrosynthesis of these compounds (6a–b) has been successfully performed on carbon rod electrodes in an undivided cell in good yield and purity.

Graphical abstractThe electro-oxidation of hydroquinone has been studied in the presence of thiouracil derivatives as nucleophiles. The results confirm the synthesis of new hydroquinonethioethers via the EC mechanism.Figure optionsDownload full-size imageDownload as PowerPoint slide