Palladium-Catalyzed Syntheses of C3-Symmetric 9-Aryl Acridine Derivatives

doi:10.6023/cjoc201707007

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 416-424.DOI: 10.6023/cjoc201707007 Previous Articles Next Articles

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钯催化C₃-对称9-芳基吖啶类衍生物的合成

董坤, 李秋云, 安康, 马俊逸, 白中胜, 刘乾才

华东师范大学化学与分子工程学院上海 200241

收稿日期:2017-07-06 修回日期:2017-09-23 发布日期:2017-10-11
通讯作者: 刘乾才 E-mail:9cliu@chem.ecnu.edu.cn

Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives

Dong Kun, Li Qiuyun, An Kang, Ma Junyi, Bai Zhongsheng, Liu Qiancai

School of Chemistry and Molecular and Engineering, East China Normal University, Shanghai 200241

Received:2017-07-06 Revised:2017-09-23 Published:2017-10-11
Contact: 10.6023/cjoc201707007 E-mail:9cliu@chem.ecnu.edu.cn

1. Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives.PDF(1583KB)

Abstract

A multiple synthetic strategy is employed to furnish the synthesis of 6, 12, 18-triaryldibenzo[b, j]quinoline[2, 3-f] [1, 7]phenanthroline. The key intermediate 6, 12, 18-trichlorobenzotriquinoline was prepared by Buchwald-Hartwig reaction of 1, 3, 5-tribromobenzene with methyl anthranilate, followed by hydrolysis and POCl₃-promoted ring closure reaction. The palladium-catalyzed Suzuki coupling was carried out with a novel catalyst Pd-132 to form fourteen C₃-symmetric 9-aryl acridine derivatives. The reactions can be performed at low catalyst loading (0.1 mol%, ca. 0.03 mol% per site).

Key words: Buchwald-Hartwig reaction, acridine, Pd-132, Suzuki coupling

Cite this article

Dong Kun, Li Qiuyun, An Kang, Ma Junyi, Bai Zhongsheng, Liu Qiancai. Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives[J]. Chin. J. Org. Chem., 2018, 38(2): 416-424.

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钯催化C₃-对称9-芳基吖啶类衍生物的合成

Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives

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钯催化C3-对称9-芳基吖啶类衍生物的合成