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

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)988-998
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number5
DOIs
Publication statusPublished - 2020 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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