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One‐Pot Synthesis of 3‐Aryl‐5‐amino‐1,2,4‐thiadiazoles from Imidates and Thioureas by I 2 ‐Mediated Oxidative Construction of the N–S Bond
Author(s) -
Chai Ling,
Lai Zhenzhen,
Xia Qiangqiang,
Yuan Jiangpei,
Bian Qilong,
Yu Mingjian,
Zhang Wenkai,
Xu Yuanqing,
Xu Hao
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800670
Subject(s) - thiadiazoles , chemistry , aryl , nucleophile , nucleophilic addition , oxidative phosphorylation , combinatorial chemistry , amino acid , base (topology) , medicinal chemistry , organic chemistry , catalysis , biochemistry , mathematical analysis , alkyl , mathematics
A simple and practical method for the one‐pot synthesis of 3‐aryl‐5‐amino‐1,2,4‐thiadiazoles from imidates and thioureas has been developed. The protocol proceeds through sequential base‐mediated nucleophilic addition‐elimination reactions and an I 2 ‐mediated oxidative coupling for the N–S bond formation. The approach employes readily available and nontoxic substrates and a simple workup to provide 3‐aryl‐5‐amino‐1,2,4‐thiadiazoles that have a free or substituted amino group.