Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 31, Pages 4338-4344Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800670
Keywords
Synthetic methods; Heterocycles; Cyclization; Imidates; Thioureas
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Funding
- National Natural Science Foundation of China [21502042, 51403051]
- Scientific Research Key Project Fund of Henan Provincial Education Department [15A150041, 16A150003]
- Scientific Research Fund of Henan University [2013YBZR008]
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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.
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