One‐Pot Synthesis of 3‐Aryl‐5‐amino‐1,2,4‐thiadiazoles from Imidates and Thioureas by I2‐Mediated Oxidative Construction of the N–S Bond

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 I2‐mediated oxidative coupling for the N–S bond forma...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-08, Vol.2018 (31), p.4338-4344
Main Authors: Chai, Ling, Lai, Zhenzhen, Xia, Qiangqiang, Yuan, Jiangpei, Bian, Qilong, Yu, Mingjian, Zhang, Wenkai, Xu, Yuanqing, Xu, Hao
Format: Article
Language:English
Subjects:
Aromatic compounds
Cyclization
Heterocycles
Imidates
Substrates
Synthesis
Synthetic methods
Thiadiazoles
Thioureas
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Summary: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 I2‐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. 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 I2‐mediated oxidative coupling for the N–S bond formation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800670