Electrochemical synthesis of 1, 2, 4-oxadiazoles from amidoximes through dehydrogenative cyclization. Issue 48 (2nd December 2021)

• Record Type: Journal Article
• Authors: Jiang, Chan; Li, Mingfang; Xu, Leitao; Yi, Yangjie; Ye, Jiao; Hu, Aixi
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 48(2021)
• Page Start: 10611
• Page End: 10616
• Publication Date: 2021-12-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02040d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The iminoxy radical generated through anodic oxidation from amidoximes undergoes 1, 5-HAT and intramolecular cyclization to obtain 1, 2, 4-oxadiazoles in good to high yields. Abstract : A convenient and efficient method for the generation of the iminoxy radical through anodic oxidation was developed for the synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazoles from N -benzyl amidoximes. The transformation proceeds through 1.5-Hydrogen Atom Transfer (1, 5-HAT) and intramolecular cyclization. The process features simple operation, mild conditions, broad substrate scope and high functional group compatibility, and provides a facile and practical way for the preparation of 1, 2, 4-oxadiazoles.