Base-catalyzed monofunctionalization of N-alkyl activated azaarenes to construct 2-Iminoderivatives. (26th January 2023)

• Record Type: Journal Article
• Authors: Duan, Dehao; Cai, Fangyuan; Wu, Yi; Gong, Quan; Huang, Aiqiong; Yi, Dongcheng; Li, Yinbao; Lai, Yingzhen; Peng, Xiang-Jun
• Is Part Of: Tetrahedron. Volume 131(2023)
• Publication Date: 2023-01-26
• Subjects: Base-catalyzed strategy -- 2-Sulfonylimin quinolines and pyridines -- Metal-free -- Monofunctionalization -- N-methylene iminium salts; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133229
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient and simple synthesis of various N -sulfonylimino quinolines and pyridines had been achieved via monofunctionalization of quinoliniums and pyridiniums, which could regioselectively favor in nucleophilic attack at the C-2 position. This base-promoted methodology has been directly to form the 2-sulfonylimino derivatives with simple available starting materials, metal-free conditions, and high regioselectivity. Graphical abstract: We have successfully discovered a base-catalyzed one-pot amidation of quinoliniums, pyridiniums and sulfonyl azides, which enabled the synthesis of a wide range of 2-imino-quinolines and pyridines with excellent synthetic efficiency in metal-free systems. Image 1