Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2196-2204.DOI: 10.6023/cjoc201305027 Previous Articles     Next Articles



魏柏松a, 谷文a,b, 徐徐a,b, 杨益琴c, 王石发a,b   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 江苏省生物质绿色燃料与化学品重点实验室 南京 210037;
    c 南京林业大学轻工科学与工程学院 南京 210037
  • 收稿日期:2013-05-15 修回日期:2013-06-06 出版日期:2013-10-25 发布日期:2013-06-21
  • 通讯作者: 王石发
  • 基金资助:

    国家自然科学基金(No. 31170538)资助项目

Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

Wei Baisonga, Gu Wena,b, Xu Xua,b, Yang Yiqinc, Wang Shifaa,b   

  1. 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:2013-05-15 Revised:2013-06-06 Online:2013-10-25 Published:2013-06-21
  • Supported by:

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

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 2a2f. Pinanyl-2-aminopyrimidines 3a3e and pinanyl isoxazolines 4a4d 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 3a3e and pinanyl isoxazolines 4a4d 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