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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1582-1586. 上一篇    下一篇

研究论文

2-芳氧基-3-对氟苯基-3,5,6,7-四氢-4H-环戊二烯并[4,5]噻吩并[2,3-d]-嘧啶-4-酮衍生物的合成及其抑菌活性

廖全斌*,a   刘明国a   喻 兰a   朱 敏a   丁明武b   

  1. (a三峡大学化学与生命科学学院 天然产物研究与利用湖北省重点实验室 宜昌 443002) (b华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079)
  • 收稿日期:2008-11-23 修回日期:2009-02-23 发布日期:2009-05-15

Synthesis and Bacteriostatic Activities of 2-Aryloxy-3-(4-fluorophenyl)- 3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]-pyrimidin-4-ones

Liao, Quanbin*,a   Liu, Mingguoa   Yu, Lana   Zhu, Mina   Ding, Mingwub   

  1. (a Hubei Provincial Key Laboratory of Natural Products Research and Development, College of Chemistry & Life Science, China Three Gorges Universtry, Yichang 443002) (b Key Laboratory of Pesticide & Chemical Biology, Ministry of Eduction, College of Chemistry, Central China Normal University, Wuhan 430079)
  • Received:2008-11-23 Revised:2009-02-23 Published:2009-05-15

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1271

被引次数

22

利用三组分氮杂Wittig反应, 以三氢环戊二烯并噻吩基三苯基膦亚胺、对氟苯基异氰酸酯和酚, 合成了13个未见文献报道的2-芳氧基-3-对氟苯基-3,5,6,7-四氢-4H-环戊二烯并[4,5]噻吩并[2,3-d]-嘧啶-4-酮衍生物, 产率58%～73%. 通过IR, 1H NMR, MS 和元素分析对目标化合物的结构进行了表征. 初步探讨了所合成化合物的抑菌活性, 结果显示所合成的化合物对真菌(桔青霉菌)的抑制活性优于对细菌的抑制活性.

关键词: 噻吩并嘧啶酮, 氮杂Wittig反应, 合成, 抑菌活性

Thirteen new 2-aryloxy-3-(4-fluorophenyl)-3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]- pyrimidin-4-ones were synthesized in 58%～73% yields by aza-Wittig reaction of (4,5,6-trihydrocyclopenta- thiophen-2-ylimino)(triphenyl)phosphorane with 4-fluorophenyl iso-cyanate，and subsequent reaction with phenols. Their structures were confirmed by IR, 1H NMR, MS techniques and elemental analyses. Their bacteriostatic activities were tested and the results showed that their bacteriostatic activities against fungus (Penicillium citrinum Thom) were better than those against bacteria.

Key words: thienopyrimidinone, aza-Wittig reaction, synthesis, bacteriostatic activity