Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 212-216.DOI: 10.6023/cjoc201407013 Previous Articles     Next Articles



林春花a, 许招会a, 廖维林b, 邱曾烨b, 夏剑辉b   

  1. a 江西师范大学化学化工学院 南昌 330027;
    b 国家单糖化学合成工程技术研究中心 南昌 330027
  • 收稿日期:2014-07-09 修回日期:2014-10-10 发布日期:2014-10-13
  • 通讯作者: 许招会, 夏剑辉
  • 基金资助:

    国家科技攻关计划(No. 2001BA323C)和江西省研究生创新基金(No. YC10A51)资助项目.

Solvent-Free One-Pot Three-Component Synthesis of 5-[(Indol-3-yl)-methyl]-2,2-butylidene-1,3-dioxane-4,6-dione Derivatives with B(OH)3 as Catalyst

Lin Chunhuaa, Xu Zhaohuia, Liao Weilinb, Qiu Zengyeb, Xia Jianhuib   

  1. a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027;
    b National Monosaccharides Chemical Synthesis Engineering Research Center, Nanchang 330027
  • Received:2014-07-09 Revised:2014-10-10 Published:2014-10-13
  • Supported by:

    Project supported by the National Science and Technology Project (No. 2001BA323C) and the Graduate Innovation Foundation of Jiangxi Province (No. YC10A51).

Nine kinds of 5-[(indol-3-yl)-methyl]-2,2-butylidene-1,3-dioxane-4,6-dione derivatives were synthesized by the three-component one-pot reaction of indole with aldehydes and 2,2-butylidene-1,3-dioxane-4,6-dione in the presence of boric acid under solvent-free. The results indicated that the yields ranged from 68.6% to 91.3%, when using 5 mol% boric acid and reacting at 60 ℃ for 30~90 min. Furthermore, a proposed reaction mechanism for the reaction catalyzed by boric acid was speculated. The main advantages of the present procedure were milder conditions, shorter reaction time and higher yields. Further study showed that boric acid was environmentally friendly and reused for six times without any noticeable decrease in the catalytic activity.

Key words: three-component reaction, one-pot synthesis, 5-[(indol-3-yl)-methyl]-2,2-butylidene-1,3-dioxane-4,6-dione, B(OH)3-promoted