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. 2022 Jul 25;61(30):e202206058.
doi: 10.1002/anie.202206058. Epub 2022 Jun 14.

Electrochemical Migratory Cyclization of N-Acylsulfonamides

Zhaojiang Shi  1 , Yuanyuan Li  2 , Nan Li  1 , Wei-Zhen Wang  1 , Hao-Kuan Lu  1 , Hong Yan  1 , Yaofeng Yuan  1 , Jun Zhu  2 , Ke-Yin Ye  1
Affiliations

Electrochemical Migratory Cyclization of N-Acylsulfonamides

Zhaojiang Shi et al. Angew Chem Int Ed Engl. .

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.

Keywords: De-aromatization; Electrochemistry; Radical; Smiles Rearrangement; Sulfonamide.

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