Citation: Chen Wen, Yuan Rui, Fang Yue, Dong Hongrui, Yasen Bumaryam, Su Liujuan, Ren Xuanxuan, Zhou Hang, Wan Yu, Zhang Peng, Zhou Shengliang, Wu Hui. Preparation and Application in the Synthesis of 4H-Chromeno-[2, 3-b]pyridine-3-carbonitriles of Tröger's Base Derivatives[J]. Chinese Journal of Organic Chemistry, ;2020, 40(4): 988-996. doi: 10.6023/cjoc201908029 shu

Preparation and Application in the Synthesis of 4H-Chromeno-[2, 3-b]pyridine-3-carbonitriles of Tröger's Base Derivatives

Chen Wen ^a,† ,
Yuan Rui ^b,† ,
Fang Yue ^a ,
Dong Hongrui ^a ,
Yasen Bumaryam ^a ,
Su Liujuan ^a ,
Ren Xuanxuan ^a ,
Zhou Hang ^a ,
Wan Yu ^b ,
Zhang Peng ^c,, ,
Zhou Shengliang ^b,, ,
Wu Hui ^b,,

a.
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b.
Key Laboratory of Biotechnology for Medicinal Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, Jiangsu 221116
c.
School of Life Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Corresponding author: Zhang Peng, zhangpeng@jsnu.edu.com Zhou Shengliang, zhousl@jsnu.edu.cn Wu Hui, wuhui72@jsnu.edu.cn

^†

Received Date: 21 August 2019
Revised Date: 16 November 2019
Available Online: 11 December 2019
Fund Project: the Graduate Student Scientific Research Innovation Projects in Jiangsu Province KYCX18_2116the Aid Project for Ph.D. Faculties in Jiangsu Normal University 17XLR023the Science and Technology Foundation of Xuzhou City KC19242Project supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Natural Science Research Projects in Universities of Jiangsu Province (No.19KJB430019), the Science and Technology Foundation of Xuzhou City (No. KC19242), the Aid Project for Ph.D. Faculties in Jiangsu Normal University (No. 17XLR023) and the Graduate Student Scientific Research Innovation Projects in Jiangsu Province (Nos. KYCX18_2111, KYCX18_2116)the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Natural Science Research Projects in Universities of Jiangsu Province 19KJB430019the Graduate Student Scientific Research Innovation Projects in Jiangsu Province KYCX18_2111

Figures(4)

A series of Schiff base catalysts (4) derived from Tröger's base-NH₂ were synthesized and used to promote the multi-component reactions of substituted salicylaldehydes, malononitrile and substituted 2-mercaptoimidazole to afford 5-(1H-imidazol-2-ylthio)-2, 4-diamino-5H-chromeno[2, 3-b]pyridine-3-carbonitrile derivatives (8) efficiently. The reaction mechanism was discussed based on the ¹H NMR analysis preliminarily. Most of products showed high inhibitory on the human breast adenocarcinoma cell (MCF-7) and adenocarcinomic human alveolarbasal epithelial cell (A549). 5-(1H-Imidazol-2-ylthio)-2, 4-diamino-7-fluoro-5H-chromeno[2, 3-b]pyridine-3-carbonitrile has antibacterial activity against Staphylococcus aureus (wild type) and Escherichia coli (wild type). The results expanded the application of Tröger's bases in organocatalysis and showed the potential of products in new drug development.
- Tröger's base,
- organoatalysis,
- chromeno[2, 3-b]pyridine,
- biological activity
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