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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 6: 1218 - 1221

DOI: https://doi.org/10.6023/cjoc201401019

Notes

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

  • Zhao Yunhui ,
  • Ren Xinfang ,
  • Liu Hanwen ,
  • Tang Zilong
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  • a. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;
    b. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education of China, Human University of Science and Technology, Xiangtan 411201, China

Received date: 2014-01-11

  Revised date: 2014-02-12

  Online published: 2014-03-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372070), the Science Foundation of Hunan Province (No. 11JJ3016) and the Hunan Provincial Education Office Scientific Research Foundation Project (No. B31314).

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Abstract

Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new (R,E)-N-(2-hydroxybenzylidene)-tert-butyl-sulfinamides (3) were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO4/PhMe or Cs2CO3/CH2Cl2. And the results show that the KHSO4/PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs2CO3/CH2Cl2 reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by 1H NMR, 13C NMR, IR and HRMS.

Key words： microwave irradiation; chiral imine; (R)-tert-butylsulfinamide; salicylaldehyde

Cite this article

Zhao Yunhui , Ren Xinfang , Liu Hanwen , Tang Zilong . Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1218 -1221 . DOI: 10.6023/cjoc201401019

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