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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 1: 212 - 216

DOI: https://doi.org/10.6023/cjoc201407013

Notes

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 Chunhua ,
  • Xu Zhaohui ,
  • Liao Weilin ,
  • Qiu Zengye ,
  • Xia Jianhui
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  • a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027;
    b National Monosaccharides Chemical Synthesis Engineering Research Center, Nanchang 330027

Received date: 2014-07-09

  Revised date: 2014-10-10

  Online 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).

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Abstract

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

Cite this article

Lin Chunhua , Xu Zhaohui , Liao Weilin , Qiu Zengye , Xia Jianhui . 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[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 212 -216 . DOI: 10.6023/cjoc201407013

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