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

doi:10.6023/cjoc201407013

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

Notes

硼酸催化三组分无溶剂“一锅法”合成5-[(3-吲哚基)-甲基]-2,2-亚丁基-1,3-二噁烷-4,6-二酮衍生物

林春花^a, 许招会^a, 廖维林^b, 邱曾烨^b, 夏剑辉^b

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 E-mail:gotoxzh@163.com
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 Chunhua^a, Xu Zhaohui^a, Liao Weilin^b, Qiu Zengye^b, Xia Jianhui^b

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).

1. 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.PDF(329KB)

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

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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]. Chin. J. Org. Chem., 2015, 35(1): 212-216.

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硼酸催化三组分无溶剂“一锅法”合成5-[(3-吲哚基)-甲基]-2,2-亚丁基-1,3-二噁烷-4,6-二酮衍生物

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

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