Electrochemical Migratory Cyclization of N‐Acylsulfonamides. (15th June 2022)

• Record Type: Journal Article
• Authors: Shi, Zhaojiang; Li, Yuanyuan; Li, Nan; Wang, Wei‐Zhen; Lu, Hao‐Kuan; Yan, Hong; Yuan, Yaofeng; Zhu, Jun; Ye, Ke‐Yin
• Is Part Of: Angewandte Chemie. Volume 134:Number 30(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-15
• Subjects: De-aromatization -- Electrochemistry -- Radical -- Smiles Rearrangement -- Sulfonamide; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202206058
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Benzoxathiazine dioxide, as a bioisostere of the clinically widely used diazoxide, exhibits interesting biological activity. However, limited success has been achieved in terms of its concise and direct synthesis. We report herein a facile electrochemical migratory cyclization of N ‐acylsulfonamides to access a diverse array of benzoxathiazine dioxides. The inclusion of electrochemistry is crucial for realizing such a novel transformation, which is substantiated both by the experiments and density‐functional‐theory calculations. Abstract : Electrochemical migratory cyclization of N ‐acylsulfonamides has been developed for the facile preparation of a diverse array of biologically interesting yet synthetically challenging benzoxathiazine dioxides.