Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides

Veerababurao Kavala, Chen Yu Wang, Cheng Chuan Wang, Prakash Bhimrao Patil, Chia Chi Fang, Chun Wei Kuo, Ching Fa Yao

研究成果: 雜誌貢獻文章

摘要

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.

原文英語
頁(從 - 到)988-998
頁數11
期刊Organic and Biomolecular Chemistry
18
發行號5
DOIs
出版狀態已發佈 - 2020 一月 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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