Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring

doi:10.6023/cjoc201301009

Chin. J. Org. Chem. ›› 0, Vol. ›› Issue (0): 0-0.DOI: 10.6023/cjoc201301009

Notes

含苯并咪唑环二酰肼衍生物的合成与结构表征

李英俊^a, 于洋^a, 许永廷^b, 靳焜^c, 罗潼川^a, 邵昕^a, 史相玲^a, 吴疆红^a

a 辽宁师范大学化学化工学院大连116029;
b 辽宁师范大学分析测试中心大连116029;
c 大连理工大学精细化工国家重点实验室大连116012

出版日期:2013-12-31 发布日期:2013-03-07
通讯作者: 李英俊 E-mail:chemlab.lnnu@163.com

Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring

Li Yingjun^a, Yu Yang^a, Xu Yongting^b, Jin Kun^c, Luo Tongchuan^a, Shao Xin^a, Shi Xiangling^a, Wu Jianghong^a

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

Online:2013-12-31 Published:2013-03-07
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

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 its 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

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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]. Chin. J. Org. Chem., 0, (0): 0-0.

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[1] Demirayak, S.; Kayagil, I.; Yurttas, L. Eur. J. Med. Chem. 2011, 46, 411.

[2] Woo, H. B.; Eom, Y. W.; Park, Kyu-Sang; 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.; Sch?chtele, C.; Kubbutat, M. H. G.; Kunick, C. Eur. J. Med. Chem. 2011, 46, 2759.

[8] Hearn, M. J.; Cynamon, M. H. Drug Design and 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.)

含苯并咪唑环二酰肼衍生物的合成与结构表征

Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring

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