Citation: Dong Kun, Li Qiuyun, An Kang, Ma Junyi, Bai Zhongsheng, Liu Qiancai. Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 416-424. doi: 10.6023/cjoc201707007 shu

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

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

Corresponding author: Liu Qiancai, 9cliu@chem.ecnu.edu.cn
Received Date: 6 July 2017
Revised Date: 23 September 2017
Available Online: 11 February 2017

Figures(7)

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).
- Buchwald-Hartwig reaction,
- acridine,
- Pd-132,
- Suzuki coupling
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Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives