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

doi:10.6023/cjoc201908029

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 988-996.DOI: 10.6023/cjoc201908029 Previous Articles Next Articles

朝格尔碱衍生物的制备及其催化的4H-色烯并[2,3-b]吡啶-3-腈的合成

陈雯^a, 苑睿^b, 房越^a, 董宏瑞^a, 布麦热叶木·亚生^a, 苏柳娟^a, 任璇璇^a, 周杭^a, 宛瑜^b, 张鹏^c, 周生亮^b, 吴翚^b

a 江苏师范大学化学与材料科学学院江苏徐州 221116;
b 江苏师范大学江苏省药用植物生物技术重点实验室江苏徐州 221116;
c 江苏师范大学生命科学学院江苏徐州 221116

收稿日期:2019-08-21 修回日期:2019-11-16 发布日期:2020-05-06
通讯作者: 吴翚, 张鹏, 周生亮 E-mail:wuhui72@jsnu.edu.cn;zhangpeng@jsnu.edu.com;zhousl@jsnu.edu.cn
基金资助:
江苏省高校优势学科建设工程、江苏省高等学校自然科学研究（No.19KJB430019）、徐州市科技计划项目（No.KC19242）、江苏师范大学博士学位教师科研支持（No.17XLR023）和江苏省研究生科研创新计划（Nos.KYCX18_2111，KYCX18_2116）资助项目.

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, Hui Wu^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

Received:2019-08-21 Revised:2019-11-16 Published:2020-05-06
Supported by:
Project 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).

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Abstract

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.

Key words: Tröger's base, organoatalysis, chromeno[2,3-b]pyridine, biological activity

Cite this article

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

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朝格尔碱衍生物的制备及其催化的4H-色烯并[2,3-b]吡啶-3-腈的合成

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

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