Electrochemical Desulfurative Cyclization Accessing Oxazol-2-amine Derivatives via Intermolecular C–N/C–O Bond Formation

A practical protocol has been established to access diverse oxazol-2-amine derivatives in one step via the electrochemical desulfurative cyclization of isothiocyanates and α-amino ketones. On the basis of the cycle of in situ generation of iodine/desulfurative cyclization/iodide anion regeneration,...

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Bibliographic Details
Published in:Organic letters 2021-02, Vol.23 (3), p.1016-1020
Main Authors: Hu, Jinhui, Hong, Huanliang, Qin, Yongwei, Hu, Yunfei, Pu, Suyun, Liang, Gen, Huang, Yubing
Format: Article
Language:English
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Summary:A practical protocol has been established to access diverse oxazol-2-amine derivatives in one step via the electrochemical desulfurative cyclization of isothiocyanates and α-amino ketones. On the basis of the cycle of in situ generation of iodine/desulfurative cyclization/iodide anion regeneration, the reaction is performed under metal-free and external-oxidant-free electrolytic conditions to achieve the formation of intermolecular C–O and C–N bonds, providing oxazol-2-amines in moderate to excellent yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04218