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External oxidant-free electrooxidative intramolecular S-N bond formation for one-pot synthesis for 3,5-disubstituted 1,2,4-thiadiazoles
Phosphorus, Sulfur, and Silicon and the Related Elements ( IF 1.4 ) Pub Date : 2020-06-12 , DOI: 10.1080/10426507.2020.1768093
Qihao Zhong 1 , Shouri Sheng 1 , Junmin Chen 1, 2
Affiliation  

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

中文翻译:

用于一锅法合成3,5-二取代1,2,4-噻二唑的外部无氧化剂电氧化分子内SN键形成

摘要 已在未分离的电解条件下开发了用于合成 5-氨基和 3,5-二氨基取代的 1,2,4-噻二唑衍生物的电化学氧化反应方案。新开发的一锅法涉及异硫氰酸酯与脒或胍反应生成相应的亚氨基硫脲,通过电氧化分子内 SN 键的形成进一步原位环化以促进最终产物。该协议具有无金属和无外部氧化剂的方法、广泛的底物范围、良好的官能团耐受性、优异的产量和一锅操作/反应,无需隔离中间体。图形概要
更新日期:2020-06-12
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