External oxidant-free electrooxidative intramolecular S-N bond formation for one-pot synthesis for 3, 5-disubstituted 1, 2, 4-thiadiazoles. (1st December 2020)

• Record Type: Journal Article
• Authors: Zhong, Qihao; Sheng, Shouri; Chen, Junmin
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 195:Number 12(2020)
• Page Start: 988
• Page End: 993
• Publication Date: 2020-12-01
• Subjects: Metal-free -- electrooxidative -- intramolecular S-N bond formation -- 3, 5-disubstituted 1, 2, 4-thiadiazole; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2020.1768093
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: An electrochemical oxidative reaction protocol for the synthesis of 5-amino and 3, 5-diamino substituted 1, 2, 4-thiadiazole derivatives has been developed under undivided electrolytic conditions. The newly developed one-pot methodology involves the reaction of isothiocyanates with amidines or guanidines to give the corresponding imidoyl thioureas, which are further cyclized in situ via electrooxidative intramolecular S-N bond formation to promote the final products. This protocol features a metal- and external oxidant-free approach, broad substrate scope, good functional group tolerance, excellent yields, and one-pot operation/reaction without the isolation of the intermediates. Graphical Abstract: UF0001