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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (23): 2835-2842.DOI: 10.6023/A1106131 上一篇    下一篇

研究论文

含三唑结构的新型稠合三环2(5H)-呋喃酮衍生物的合成

李建晓, 汪朝阳*, 薛福玲, 罗时荷   

  1. (华南师范大学化学与环境学院 广州 510006)
  • 投稿日期:2011-06-13 修回日期:2011-08-06 发布日期:2011-08-25
  • 通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
  • 基金资助:

    国家自然科学基金

Synthesis of Novel Tricyclic Fused 2(5H)-Furanone Derivatives with 1,2,3-Triazole Structure

LI Jian-Xiao, WANG Chao-Yang, XUE Fu-Ling, LUO Shi-He   

  1. (School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
  • Received:2011-06-13 Revised:2011-08-06 Published:2011-08-25
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

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利用系列含烯二炔结构的2(5H)-呋喃酮衍生物与叠氮化钠发生串联的成环反应, 在优化的反应条件下, 即反应溶剂为DMF、反应时间48 h、反应温度30 ℃时、NaN3为1.5 equiv., 以中等产率(42%～62%)合成了系列新型的稠合三环2(5H)-呋喃酮衍生物, 其可以进一步高产率地(94%～96%)衍生为吡啶稠合的2(5H)-呋喃酮化合物. 所有新化合物的结构用IR, 1H NMR, 13C NMR, MS, 元素分析等方法进行了表征. 该串联反应合成途径简捷、反应条件温和, 无需添加催化剂, 可为具有含三唑结构的稠杂环化合物合成提供简便的途径.

关键词: 2(5H)-呋喃酮, 烯二炔, 串联反应, 1,2,3-三唑结构

A novel tandem cyclization of 2(5H)-furanone derivatives containing enediyne structure with sodium azide giving rise to serial novel 1,2,3-triazole polycyclic compounds was accomplished. Under the optimized conditions, including 1.5 equiv. sodium azide, DMF as the solvent, the tandem reaction at 30 ℃ for 48 h gave the 2(5H)-furanone derivatives containing tricyclic structure in moderate yields (42%～62%). The tricyclic fused 2(5H)-furanone derivatives with 1,2,3-triazole structure could be converted into fused pyridine derivatives with high yields (94%～96%). The structure of all fused 2(5H)-furanone derivatives was confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. And the possible reaction mechanism of the tandem cyclization was proposed. This tandem reaction has the advantages of easy operation, mild reaction condition and without the addition of catalyst. Moreover, this method was a convenient and simple path for the synthesis of the tricyclic fused 2(5H)-furanone derivatives containing 1,2,3-triazole.

Key words: 2(5H)-furanone, enediyne structure, tandem reaction, 1,2,3-triazole structure