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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1551 - 1558

DOI: https://doi.org/10.6023/cjoc201301009

Notes

Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring

  • Li Yingjun ,
  • Yu Yang ,
  • Xu Yongting ,
  • Jin Kun ,
  • Luo Tongchuan ,
  • Shao Xin ,
  • Shi Xiangling ,
  • Wu Jianghong
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  • a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Analysis and Inspection Center, Liaoning Normal University, Dalian 116029;
    c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Received date: 2013-01-04

  Revised date: 2013-02-26

  Online published: 2013-03-07

Supported by

Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

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Abstract

Ten novel dihydrazide derivatives containing benzimidazole ring (7a～7j) were synthesized by (un)substituted phenol and chloroacetic acid as starting materials via a series of reactions. The structure of representative compound 7c was confirmed by 1H NMR, 13C NMR, 2D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and variable-temperature 1H NMR spectra. The experimental results indicate that compound 7c in DMSO at room temperature exists in the tautomeric A and B isomers, and A isomer is dominant (87.65%). On the basis of the analytic results of compound 7c, 1H NMR spectra of other target compounds were also assigned and the content of dominant A isomer is in the range of 80.55%～89.90%.

Key words： dihydrazide; synthesis; characterization

Cite this article

Li Yingjun , Yu Yang , Xu Yongting , Jin Kun , Luo Tongchuan , Shao Xin , Shi Xiangling , Wu Jianghong . Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1551 -1558 . DOI: 10.6023/cjoc201301009

References

[1] Demirayak, S.; Kayagil, I.; Yurttas, L. Eur. J. Med. Chem. 2011, 46, 411.
[2] Woo, H. B.; Eom, Y. W.; Park, K.-S.; Ham, J.; Ahn, C. M.; Lee, S. Bioorg. Med. Chem. Lett. 2012, 22, 933.
[3] Li, Y.-J.; Liu, L.-J.; Jin, K.; Sun, S.-Q.; Xu, Y.-T. Acta Chim. Sinica 2010, 68(16), 1577 (in Chinese). (李英俊, 刘丽军, 靳焜, 孙淑琴, 许永廷, 化学学报, 2010, 68(16), 1577.)
[4] Kaushik, D.; Khan, S. A.; Chawla, G. Med. Chem. Res. 2012, 21, 459.
[5] Soni, L. K.; Narsinghani, T.; Sethi, A. Med Chem Res. 2012, 21, 4330.
[6] Hernández-Luis, F.; Hernández-Campos, A.; Castillo, R.; Navarrete-Vázquez, G.; Soria-Arteche, O.; Hernández-Hernández, M.; Yépez-Muli, L. Eur. J. Med. Chem. 2010, 45, 3135.
[7] Schmidt, S.; Preu, L.; Lemcke, T.; Totzke, F.; Schächtele, C.; Kubbutat, M. H. G.; Kunick, C. Eur. J. Med. Chem. 2011, 46, 2759.
[8] Hearn, M. J.; Cynamon, M. H. Drug Des. Discovery 2003, 18, 103.
[9] Thomas, K. D.; Adhikari, A. V.; Telkar, S.; Telkar, S.; Chowdhury, I. H.; Mahmood, R.; Pal, N. K.; Row, G.; Sumesh, E. Eur. J. Med. Chem. 2011, 46, 5283.
[10] Kovganko, N. V.; Ananich, S. K. Russ. J. Bioorg. Chem. 2004, 30, 505.
[11] Parra, M.; Hidalgo, P.; Barberá, J.; Carrasco, E.; Saavedra, C. Liq. Cryst. 2006, 33, 391.
[12] Li, Y.-J.; Liu, L.-J.; Jin, K.; Wang, W.; Zhao, N.; Li, L.-N.; Li, C.-Y. Chin. J. Org. Chem. 2009, 29(11), 1825 (in Chinese). (李英俊, 刘丽军, 靳焜, 王巍, 赵楠, 李丽娜, 李春燕, 有机化学, 2009, 29(11), 1825.)
[13] Li, L.-N. M.S. Thesis, Liaoning Normal University, Dalian, 2011 (in Chinese). (李丽娜, 硕士论文, 辽宁师范大学, 大连, 2011.)
[14] Cativiela, C.; Serrano, J. L.; Zurbano, M. M. J. Org. Chem. 1995, 60, 3074.
[15] Li, Y.-J.; Ding, W.-G.; Jin, K.; Sun, S.-Q.; Liu, J.; Liu, L.-J.; Wang, J.-K. Chin. J. Org. Chem. 2009, 29(1), 82 (in Chinese). (李英俊, 丁万刚, 靳焜, 孙淑琴, 刘军, 刘丽军, 王金奎, 有机化学, 2009, 29(1), 82.)
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