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


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   

  1. 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;;
  • 基金资助:

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

Chen Wena, Yuan Ruib, Fang Yuea, Dong Hongruia, Yasen Bumaryama, Su Liujuana, Ren Xuanxuana, Zhou Hanga, Wan Yub, Zhang Pengc, Zhou Shengliangb, Hui Wub   

  1. 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).

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