Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (23): 2835-2842.DOI: 10.6023/A1106131 Previous Articles     Next Articles

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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)
  • 收稿日期:2011-06-13 修回日期:2011-08-06 出版日期:2011-12-14 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 Online:2011-12-14 Published:2011-08-25
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

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