Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward 3-hydroxyisoindolinone derivatives. Issue 21 (20th May 2022)

• Record Type: Journal Article
• Authors: Shi, Zhaojiang; Li, Nan; Wang, Wei-Zhen; Lu, Hao-Kuan; Yuan, Yaofeng; Li, Zhen; Ye, Ke-Yin
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 21(2022)
• Page Start: 4320
• Page End: 4323
• Publication Date: 2022-05-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00637e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An electrochemical N-attacked 5- exo-dig radical cyclization of 2-alkynylbenzamides toward the synthesis of biologically relevant 3-hydroxyisoindolinone derivatives has been developed. Abstract : Preparation of biologically relevant 3-hydroxyisoindolinones from readily available 2-alkynylbenzamides is an appealing synthetic approach. However, such kinds of compounds preferably undergo O-attacked 5- exo-dig /6- endo-dig cyclizations. Herein, we report an electrochemically generated amidyl radical proceeding via a highly selective N-attacked 5- exo-dig radical cyclization to form 3-hydroxyisoindolinone derivatives. This reaction features simple operation, good selectivity, and broad substrate scope. Moreover, gram-scale preparation and synthetic elaborations imply the potential applicability of this protocol for the synthesis of diverse isoindolinone derivatives.