Citation: Yu Zutao, Wang Zeyu, Wu Xiao, Hu Gaoyun, Li Qianbin. "One-Pot" Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1672-1676. doi: 10.6023/cjoc201512007 shu

"One-Pot" Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe

Yu Zutao ^a ,
Wang Zeyu ^a ,
Wu Xiao ^b ,
Hu Gaoyun ^a ,
Li Qianbin ^a,*,,

a.
Medicinal Chemistry of Pharmacy Department, Central South University, Changsha 410013
b.
Medicine Department, Hunan Normal University, Changsha 410013

Corresponding author: Li Qianbin,
Received Date: 3 December 2015
Revised Date: 10 March 2016

Fund Project: the Specialized Research Fund for the Doctoral Program of Higher Education of China 20110162120033the National Natural Science Foundation of China 21102184

Figures(2)

An easy and efficient "one-pot" synthetic method facilitated by Fe to synthesize substituted 1-phenyl-1H-benzimi-dazole has been developed successfully. By using liquid organic acid as solvent, 2-nitro-N-phenylaniline is converted to substituted 1-phenyl-1H-benzimidazole directly after reduction and cyclization catalyzed by Fe, with the yield of 80%~92%. Through the application of high performance liquid chromatography (HPLC) detection, the effects of the amount of solvent, the type of liquid organic acid, temperature and reaction time on the "one-pot" reaction have been fully investigated, as well as the reaction mechanism. The "one-pot" method proposed here has multiple advantages, such as mild condition, easy procedure, cheap ingredients and high yield, which provide a newly convenient synthetic route.
- one-pot synthesis,
- 1-phenyl-1H-benzimidazole,
- Fe catalysis,
- reaction mechanism
1. [1]
  Kaur, G.; Kaur, M.; Silakari, O. Mini-Rev. Med. Chem. 2014, 14, 747.
2. [2]
3. [3]
  Whitehurst, C. B.; Sanders, M. K.; Law, M.; Wang, F. Z.; Xiong, J.; Dittmer, D. P.; Pagano, J. S. J. Virol 2013, 87, 5311.
4. [4]
  Hetzel, D. J.; Dent, J.; Reed, W. D.; Narielvala, F. M.; Mackinnon, M.; McCarthy, J. H.; Mitchell, B.; Beveridge, B. R.; Laurence, B. H.; Gibson, G. G.; Granta, A. K.; Shearmana, D.; Whiteheada, R.; Bucklea, P. Gastroenterology 1988, 95, 903.
5. [5]
  Satoh, H. Curr. Pharm. Design 2013, 19, 67.
6. [6]
  Horton, J. Fundam.-Clin. Pharmacol. 2003, 17, 205.
7. [7]
  Pawluk, S. A.; Roels, C. A.; Wilby, K. J.; Ensom, M. H. Clin. Pharmacokinet. 2015, 54, 371.
8. [8]
  Pech, P.; Heneberg, P. J. Invertebr. Pathol. 2015, 130, 61.
9. [9]
10. [10]
  Mukhopadhyay, C.; Tapaswi, P. K. Synth. Commun. 2012, 42, 2217.
11. [11]
  Muangpaisal, R.; Hung, W. I.; Lin, J. T.; Ting, S. Y.; Chen, L. Y. Tetrahedron 2014, 70, 2992.
12. [12]
  Ansari, K. F.; Lal, C. Eur. J. Med. Chem. 2009, 44, 4028.
13. [13]
  Sharghi, H.; Asemani, O.; Tabaei, S. M. H. J. Heterocycl. Chem. 2008, 45, 1293.
14. [14]
  Chari, M. A.; Shobha, D.; Kenawy, E. R.; Al-Deyab, S. S.; Reddy, B. V. S.; Vinu, A. Tetrahedron Lett. 2010, 51, 5195.
15. [15]
  Weires, N. A.; Boster, J.; Magolan, J. Eur. J. Org. Chem. 2012, 6508.
16. [16]
  Sekar, R.; Srinivasan, M.; Marcelis, A. T. M.; Sambandam, A. Tetrahedron Lett. 2011, 52, 3347.
17. [17]
  Zou, B. L.; Yuan, Q. L.; Ma, D. W. Angew. Chem., Int. Ed. 2007, 46, 2598.
18. [18]
  Selvam, K.; Swaminathan, M. Tetrahedron Lett. 2011, 52, 3386.
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