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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:[email protected]

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