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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 988 - 996

DOI: https://doi.org/10.6023/cjoc201908029

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

  • Chen Wen ,
  • Yuan Rui ,
  • Fang Yue ,
  • Dong Hongrui ,
  • Yasen Bumaryam ,
  • Su Liujuan ,
  • Ren Xuanxuan ,
  • Zhou Hang ,
  • Wan Yu ,
  • Zhang Peng ,
  • Zhou Shengliang ,
  • Hui Wu
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  • 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 date: 2019-08-21

  Revised date: 2019-11-16

  Online 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 . DOI: 10.6023/cjoc201908029

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