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

doi:10.6023/cjoc201512007

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1672-1676.DOI: 10.6023/cjoc201512007 Previous Articles Next Articles

Notes

铁粉促进“一锅法”合成1-苯基苯并咪唑类化合物

余祖滔^a, 王泽瑜^a, 吴肖^b, 胡高云^a, 李乾斌^a

a. 中南大学药学院药物化学系长沙 410013;
b. 湖南师范大学医学院药学长沙 410013

收稿日期:2015-12-03 修回日期:2016-03-10 发布日期:2016-03-25
通讯作者: 李乾斌 E-mail:qbli@csu.edu.cn
基金资助:
国家自然科学基金（No.21102184）和高等学校博士学科点专项科研基金（No.20110162120033）资助项目.

“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

Received:2015-12-03 Revised:2016-03-10 Published:2016-03-25
Supported by:
Project supported by the the National Natural Science Foundation of China (No. 21102184) and the Specialized Research Fund for the Doctoral Program of Higher Education of China (No. 20110162120033).

1. “One-Pot” Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe.PDF(1382KB)

Abstract

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.

Key words: one-pot synthesis, 1-phenyl-1H-benzimidazole, Fe catalysis, reaction mechanism

Cite this article

Yu Zutao, Wang Zeyu, Wu Xiao, Hu Gaoyun, Li Qianbin. “One-Pot” Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe[J]. Chin. J. Org. Chem., 2016, 36(7): 1672-1676.

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References

[1] Kaur, G.; Kaur, M.; Silakari, O. Mini-Rev. Med. Chem. 2014, 14, 747.
[2] Zhu, G. M.; Yang, L. Y.; Cui, D. M. Chin. J. Org. Chem. 2014, 34, 495 (in Chinese). (朱观明, 杨柳阳, 崔冬梅, 有机化学, 2014, 34, 495.)
[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] 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] Satoh, H. Curr. Pharm. Design 2013, 19, 67.
[6] Horton, J. Fundam.-Clin. Pharmacol. 2003, 17, 205.
[7] Pawluk, S. A.; Roels, C. A.; Wilby, K. J.; Ensom, M. H. Clin. Pharmacokinet. 2015, 54, 371.
[8] Pech, P.; Heneberg, P. J. Invertebr. Pathol. 2015, 130, 61.
[9] Cheng, Z.; Zhang, Q. F.; Xu, X. L.; Li, X. N. Chin. J. Org. Chem. 2015, 35, 1189 (in Chinese). (程正, 张群峰, 许孝良, 李小年, 有机化学, 2015, 35, 1189.)
[10] Mukhopadhyay, C.; Tapaswi, P. K. Synth. Commun. 2012, 42, 2217.
[11] Muangpaisal, R.; Hung, W. I.; Lin, J. T.; Ting, S. Y.; Chen, L. Y. Tetrahedron 2014, 70, 2992.
[12] Ansari, K. F.; Lal, C. Eur. J. Med. Chem. 2009, 44, 4028.
[13] Sharghi, H.; Asemani, O.; Tabaei, S. M. H. J. Heterocycl. Chem. 2008, 45, 1293.
[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] Weires, N. A.; Boster, J.; Magolan, J. Eur. J. Org. Chem. 2012, 6508.
[16] Sekar, R.; Srinivasan, M.; Marcelis, A. T. M.; Sambandam, A. Tetrahedron Lett. 2011, 52, 3347.
[17] Zou, B. L.; Yuan, Q. L.; Ma, D. W. Angew. Chem., Int. Ed. 2007, 46, 2598.
[18] Selvam, K.; Swaminathan, M. Tetrahedron Lett. 2011, 52, 3386.

铁粉促进“一锅法”合成1-苯基苯并咪唑类化合物

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

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