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钯催化的烯丙酰胺与2-碘苯胺的串联环化反应以合成官能化吲哚喹啉。

Palladium-catalyzed cascade cyclization of allenamide with 2-iodoanilines to access functionalized indoloquinolines.

作者信息

Geng Wenzhe, Wang Hui, Xi Juan, Jiang Ruonan, Guo Jintao, Jiao Keqiang, Tang Mengyao, Liu Qing, Zhang Lizhi, Liu Hui

机构信息

School of Chemistry & Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China.

Shandong Jincheng Biopharmaceutical Co., Ltd., No. 3 Shuangshan Road of Xingshan, Zibo 255049, P. R. China.

出版信息

Org Biomol Chem. 2023 Jan 4;21(2):279-283. doi: 10.1039/d2ob01770a.

Abstract

A novel and efficient palladium-catalyzed cascade cyclization to indoloquinoline derivatives in one pot has been developed by using allenamide derivatives and 2-iodoanilines as the key building blocks. The process involved two cyclizations: intramolecular cyclization/π-allylic substitution and intramolecular 6- Heck cyclization. Furthermore, dihydrobenzofuro[2,3-]quinoline derivatives could also be achieved this strategy using allenyl ethers instead of allenamides. The readily available substrates, mild conditions, high efficiency and step economy make this strategy a promising method in the synthesis of polycyclic motifs.

摘要

通过使用烯丙酰胺衍生物和2-碘苯胺作为关键构建块,开发了一种新颖且高效的钯催化一锅法串联环化反应,用于合成吲哚喹啉衍生物。该过程涉及两次环化反应:分子内环化/π-烯丙基取代反应和分子内6-Heck环化反应。此外,使用烯丙基醚代替烯丙酰胺,通过该策略也可以得到二氢苯并呋喃[2,3 -]喹啉衍生物。易于获得的底物、温和的条件、高效率和步骤经济性使得该策略成为合成多环结构单元的一种有前景的方法。

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