loading page

Copper-catalyzed intramolecular cyclization synthesis of 2-hydroxy-indolin-3-ones: a combined experimental and theoretical study
  • +4
  • Haojie Ma,
  • Fengyuan Zhou,
  • Yuqi Li,
  • Yuqi Zhang,
  • Guosheng Huang,
  • Xing Yang,
  • Ji-Jiang Wang
Haojie Ma
Yan'an University

Corresponding Author:mahj@yau.edu.cn

Author Profile
Fengyuan Zhou
Yan'an University
Author Profile
Yuqi Li
Yan'an University
Author Profile
Yuqi Zhang
Yan'an University
Author Profile
Guosheng Huang
Lanzhou University
Author Profile
Xing Yang
Lanzhou Institute of Chemical Physics
Author Profile
Ji-Jiang Wang
Yan'an University
Author Profile

Abstract

The synthesis of substituted 2-hydroxy-indolin-3-ones has attracted considerable attention of synthetic chemists because they present in numbers of natural products and biologically active molecules. Herein, a novel and convenient copper-catalyzed oxidative intramolecular cyclization of N-(2-acetylphenyl)picolinamide for the synthesis of 2-hydroxy-indolin-3-ones has been developed. Moreover, the detailed mechanism presented is supported by control experiments and density function-al theory calculations. This method provides direct access to 2-hydroxy-indolin-3-ones in high yield and good functional group tolerance. Atom-economy, avoidance of the preparation for substrates and step economy make this protocol be practical. This strategy provides an alternative synthetic method to ex-plore the synthetic application of various types of 2-hydroxy-indolin-3-ones and their enantiopure deriv-atives.