Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

doi:10.1007/s40242-020-9019-3

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (5): 835-842.doi: 10.1007/s40242-020-9019-3

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Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

WANG Zeyou¹, SHEN Guodong¹, HUANG Xianqiang¹, GONG Shuwen¹, YANG Bingchuan¹, SUN Zhenzhen¹, ZHANG Zuhao¹, LIU Wanxing²

1. School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, P. R. China;
2. Department of Chemistry, Liaocheng Chemical Institute of Industrial Science, Liaocheng 252000, P. R. China

Received:2019-10-24 Revised:2019-12-02 Online:2020-10-01 Published:2020-10-01
Contact: SHEN Guodong, HUANG Xianqiang E-mail:shenguodong33@163.com;hxqqxh2008@163.com
Supported by:
Supported by the Natural Science Foundation of Shandong Province, China(Nos.ZR2019QB022, ZR2019MB043).

Abstract

Abstract: We reported an economic and practical ball-milling method for the synthesis of tetrahydroquinoline derivatives via a ‘one-pot’ three-component Diels-Alder reaction of anilines, aldehydes and alkenes catalyzed by phosphotungstic acid at room temperature. For this reaction, a simple ‘one-pot’ ball-milling operation was conducted, readily available starting materials were employed, ‘one-pot’ conditions were applied, and the most important was to use inexpensive and environmentally friendly catalyst phosphotungstic acid. Various tetrahydroquinolines, which might be potentially applicable in the pharmaceutical and biochemical areas, were conveniently synthesized in mo-derate to excellent yields.

Key words: Ball-milling, Diels-Alder reaction, Phosphotungstic acid, Tetrahydroquinoline

WANG Zeyou, SHEN Guodong, HUANG Xianqiang, GONG Shuwen, YANG Bingchuan, SUN Zhenzhen, ZHANG Zuhao, LIU Wanxing. Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid[J]. Chemical Research in Chinese Universities, 2020, 36(5): 835-842.

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Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

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