由苯胺和炔酸酯无溶剂机械合成多取代1,2-二氢喹啉
Solvent-Free Mechanosynthesis of Polysubstituted 1,2-Dihydroquinolines from Anilines and Alkyne Esters.
作者信息
Xu Hui, Wang Guan-Wu
机构信息
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. China.
出版信息
J Org Chem. 2022 Jul 1;87(13):8480-8491. doi: 10.1021/acs.joc.2c00605. Epub 2022 Jun 22.
A novel one-pot reaction of anilines with acetylenedicarboxylate diesters in the presence of boron trifluoride, iodine, and trifluoroacetic acid or methylsulfonic acid has been developed under solvent-free ball-milling conditions, affording a variety of polysubstituted 1,2-dihydroquinolines bearing multiple ester groups in moderate to excellent yields. The present protocol features mild reaction conditions, short reaction time, and feasibility of large-scale synthesis, providing a facile and practical alternative to 1,2-dihydroquinoline synthesis. Intriguingly, the generated 1,2-dihydroquinolines can be further transformed into quinoline derivatives.
在无溶剂球磨条件下，开发了一种新颖的苯胺与乙炔二羧酸二酯在三氟化硼、碘以及三氟乙酸或甲磺酸存在下的一锅法反应，可中等至优异产率地得到多种带有多个酯基的多取代1,2 - 二氢喹啉。本方法具有反应条件温和、反应时间短以及大规模合成可行性的特点，为1,2 - 二氢喹啉的合成提供了一种简便实用的替代方法。有趣的是，生成的1,2 - 二氢喹啉可进一步转化为喹啉衍生物。
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