An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

• Published in: Journal of environmental chemical engineering 2022-06, Vol.10 (3), p.107487, Article 107487
• Main Authors: Li, Pei, Yang, Shang-Feng, Fang, Zi-Lin, Cui, Hao-Ran, Liang, Sen, Tian, Hong-Yu, Sun, Bao-Guo, Zeng, Cheng-Chu
• Format: Article
• Language: English
• Subjects: 2-Amniothiazoles; Indirect electrolysis; Organic electrosynthesis; α-C-H functionalization
• ISSN: 2213-3437; 2213-3437
• DOI: 10.1016/j.jece.2022.107487

An efficient one-pot electrochemical protocol for the synthesis of 2-aminothiazoles has been described from electrolysis of ketones with thioureas mediated by iodide ion. The electrochemical synthesis was conducted in an undivided cell equipped with graphite plates electrodes under constant current conditions. A diversity of aromatic and aliphatic ketones was suitable for the reaction, yielding the corresponding 2-aminothiazoles in satisfactory yields. Mechanistically, the in-situ generated α-iodoketone was proposed to be a key active species. [Display omitted] •An efficient one pot electrochemical synthesis of 2-aminothiazoles from ketones and thioureas mediated by iodide is described.•The environmentally benign approach proceeds in an undivided cell without additional oxidants and metal catalysts.•Mechanistically, the in-situ generated α-iodoketones was proposed to be the key active species.•The method can be readily carried out in gram-scale and successfully applied to the synthesis of Fanetizole.