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A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement

  • Ye Meijun ,
  • Zhang Peizhi ,
  • Wu Jun
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  • a Hangzhou Tea Research Institute, All China Federation of Supply and Marketing Cooperatives, Hangzhou 310016;
    b School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023;
    c Department of Chemistry, Zhejiang University, Hangzhou 310027

Received date: 2016-04-10

  Revised date: 2016-06-02

  Online published: 2016-08-10

Supported by

Project supported by the Agro-scientific Research in the Public Interest (No. 201403030) and the National Natural Science Foundation of China (No. 31471807).

Abstract

Based on high performance liquid chromatography (HPLC), a fast, efficient and simple route for Smiles rearrangement reaction has been developed in the presence of 2-pyrimidinyloxy-N-arylbenzylamine derivatives as reactants with HCl as acid catalyst in mixed CH3OH/H2O medium at room temperature. The advantage of the proposed method is that the products with excellent yields and high purity can be obtained employing reused solvent without further separating process. Considering the cheapness of catalyst and solvent, as well as high efficient and environment-friendly reaction condition, the developed method has the practicability and environmentally friendliness.

Cite this article

Ye Meijun , Zhang Peizhi , Wu Jun . A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement[J]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2997 -3002 . DOI: 10.6023/cjoc201604020

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