Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides. Issue 5 (16th January 2020)

• Record Type: Journal Article
• Authors: Kavala, Veerababurao; Wang, Chen-Yu; Wang, Cheng-Chuan; Patil, Prakash Bhimrao; Fang, ChiaChi; Kuo, Chun-Wei; Yao, Ching-Fa
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 5(2020)
• Page Start: 988
• Page End: 998
• Publication Date: 2020-01-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02329a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides were achieved in one-pot two-step sequential reaction. Abstract : An efficient one-pot two-step sequential reaction for the synthesis of biologically active 3-hydroxyisoindolin-1-one derivatives from 2-iodobenzamide derivatives and various substituted benzyl cyanides in the presence of CuCl and cesium carbonate in DMSO is reported. Furthermore, 3-hydroxyisoindolinone derivatives possessing bromo substituents were obtained from 2-iodobenzamide and 2-bromobenzyl cyanide substrates in two steps. Benzyl cyanide has been successfully used for the first time as a benzoyl synthon for the synthesis of 3-hydroxyisoindolin-1-ones. Interestingly, the mechanism of formation of 3-hydroxyisoindolin-1-ones is a novel pathway that involves carbon degradation followed by ring contraction.