Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

doi:10.6023/cjoc201803007

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2761-2766.DOI: 10.6023/cjoc201803007 Previous Articles Next Articles

Notes

氯化胆碱催化醛、吲哚和丙二腈的三组分Yonemitsu缩合反应

杨中华, 刘兰野, 赵益鹤, 洪远琳, 阮鸿力, 吕成伟

辽宁师范大学化学化工学院大连 116029

收稿日期:2018-03-05 修回日期:2018-05-31 发布日期:2018-06-07
通讯作者: 吕成伟,E-mail:chengweilv@126.com E-mail:chengweilv@126.com
基金资助:
国家自然科学基金（No.21403100）和国家级大学生创新创业训练计划（No.201710165304）资助项目.

Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

Yang Zhonghua, Liu Lanye, Zhao Yihe, Hong Yuanlin, Ruan Hongli, Lü Chengwei

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Received:2018-03-05 Revised:2018-05-31 Published:2018-06-07
Contact: 10.6023/cjoc201803007 E-mail:chengweilv@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21403100), the National Students Program for Innovation and Entrepreneurship Training (No. 201710165304).

1. Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile.PDF(857KB)

Abstract

Using choline chloride as cheap and safe accelerator was efficient to promote the Yonemitsu type condensation of indole, benzaldehyde, and malononitrile. More importantly, introducing right amount of water in reaction system was crucial to get desired 3-substituted indoles in good to excellent yields. Due to the catalyst has excellent solubility in aqueous ethanol, the final concoction was easy to separate. Many desired products could be obtained after filtration and washed with cold aqueous ethanol without further purification. Catalyst could further reuse for five more reaction cycles with negligible loss in activity.

Key words: 3-substituted indoles, Yonemitsu condensation, multicomponent reactions, choline chloride, organocatalysis, synthetic methods

Cite this article

Yang Zhonghua, Liu Lanye, Zhao Yihe, Hong Yuanlin, Ruan Hongli, Lü Chengwei. Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile[J]. Chin. J. Org. Chem., 2018, 38(10): 2761-2766.

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氯化胆碱催化醛、吲哚和丙二腈的三组分Yonemitsu缩合反应

Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

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