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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 10: 2196 - 2204

DOI: https://doi.org/10.6023/cjoc201305027

Articles

Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

  • Wei Baisong ,
  • Gu Wen ,
  • Xu Xu ,
  • Yang Yiqin ,
  • Wang Shifa
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  • a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
    c College of Light Industry and Engineering, Nanjing Forestry University, Nanjing 210037

Received date: 2013-05-15

  Revised date: 2013-06-06

  Online published: 2013-06-21

Supported by

Project supported by the National Natural Science Foundation of China (No. 31170538).

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Abstract

New types of pinanyl-2-aminopyrimidines and pinanyl isoxazolines were synthesized from (-)-α-pinene. (-)-α-Pinene was selectively oxidized into (+)-2-hydroxy-3-pinanone, which was condensed with aromatic aldehydes to obtain 4-arylidene-2-hydroxy-3-pinanones 2a～2f. Pinanyl-2-aminopyrimidines 3a～3e and pinanyl isoxazolines 4a～4d were prepared by cyclization of 4-arylidene-2-hydroxy-3-pinanones with guanidine hydrochloride and hydroxylamine hydrochloride under catalysis of NaOH or t-BuOK. The structures of the synthesized compounds were determined by 1H NMR, 13C NMR, FT-IR, GC-MS, and elemental analyses. Antibacterial and antifungal activities tests of the synthesized pinanyl-2-aminopyri- midines 3a～3e and pinanyl isoxazolines 4a～4d against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. subtilis, and P. fluorescens were also carried out, and it has been observed that compounds 3b and 3e had strong antibacterial effects to E. coli and B. subtilis, 3a, 3d, 4b and 4d had good activities to E. coli.

Key words： (-)-α-pinene; 4-arylidene-2-hydroxy-3-pinanones; pinanyl-2-aminopyrimidines; pinanyl isoxazolines; antibacterial activity

Cite this article

Wei Baisong , Gu Wen , Xu Xu , Yang Yiqin , Wang Shifa . Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles[J]. Chinese Journal of Organic Chemistry, 2013 , 33(10) : 2196 -2204 . DOI: 10.6023/cjoc201305027

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