Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

doi:10.6023/cjoc201305027

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

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新型蒎烷基含氮杂环化合物的合成及抑菌活性研究

魏柏松^a, 谷文^a,b, 徐徐^a,b, 杨益琴^c, 王石发^a,b

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 发布日期:2013-06-21
通讯作者: 王石发 E-mail:wsfyyq@njfu.com.cn
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 Baisong^a, Gu Wen^a,b, Xu Xu^a,b, Yang Yiqin^c, Wang Shifa^a,b

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 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 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

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Wei Baisong, Gu Wen, Xu Xu, Yang Yiqin, Wang Shifa. Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles[J]. Chin. J. Org. Chem., 2013, 33(10): 2196-2204.

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新型蒎烷基含氮杂环化合物的合成及抑菌活性研究

Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

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