Construction of 5-Amino-1,2-Selenazole Scaffolds through N-Selenocyanation/Cyclization of Enaminones Using KSeCN
Caifeng Yuan1, Xuankun Huang1, Jianhua Guo1
1Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education and Yunnan Province Center for Research & Development of Natural Products; School of Pharmacy, Yunnan University, Kunming, 650500, P. R. China.
Abstract:
A metal-free and mild approach for constructing 5-amino-1,2-selenazole skeletons by NBS/KSeCN-mediated N-selenocyanation and nucleophilic cyclization of β-enaminones has been developed. Various isoselenazole compounds and the isoselenazolyl derivatives of anti-inflammatory medicines, including isosepac, oxaprozin, and ibuprofen, have been obtained with good yields. This efficient, "one-pot", and atomic economy strategy may represent an alternative route for the construction of a 1,2-selenazole framework via the "+SeCN" pathway and provide new access to heterocycles containing a Se-N bond.
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