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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4298 - 4304

DOI: https://doi.org/10.6023/cjoc202005087

Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines

  • Liu Xinming ,
  • Li Lu ,
  • Jin Licheng ,
  • Zhao Jincan ,
  • Hua Yuanzhao ,
  • Wang Mincan ,
  • Liu Lantao
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  • a College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000;
    b College of Chemistry & Environmental Science, Hebei University, Baoding, Hebei 071002;
    c College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received date: 2020-05-29

  Revised date: 2020-07-02

  Online published: 2020-07-23

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572126), the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011), the Natural Science Foundation of Hebei Province (No. B2019201415), and the Fundamental Research Funds for the Midwest Universities Comprehensive Strength Promotion Project (No. 521000981026).

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Abstract

With inexpensive potassium halide (KX) as halogen source, and oxone as oxidant, a series of allylamides underwent halocyclization reaction and generated 5-halomethyl-2-oxazolines in good to excellent isolated yields under mild conditions. The protocol showed attractive advanced features including low cost of halogen source, absence of organic byproduct, and resultant environmental-friendly nature. In addition, various useful derivatives could be expected by proper nucleophilic substitution reactions.

Key words： oxone; halocyclization; oxazolines

Cite this article

Liu Xinming , Li Lu , Jin Licheng , Zhao Jincan , Hua Yuanzhao , Wang Mincan , Liu Lantao . Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4298 -4304 . DOI: 10.6023/cjoc202005087

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