苯并咪唑类化合物催化合成的研究进展

doi:10.6023/cjoc201411031

摘要/Abstract

苯并咪唑类化合物在医药、农药等方面具有广泛的应用, 因此这类化合物合成的新方法备受关注. 从合成苯并咪唑类化合物的不同的原料出发, 综述了近年来催化合成苯并咪唑化合物的研究新进展.

Benzimidazole compounds are widely used in the field of medicine and pesticide, so new methods for the synthesis of these compounds have attracted enormous attentions worldwide. The recent advance in the synthetic method of benzimidazole compounds based on different raw materials is reviewed.

Key words: benzimidazole, o-phenylenediamine, synthesis, catalyst

引用此文

程正, 张群峰, 许孝良, 李小年. 苯并咪唑类化合物催化合成的研究进展[J]. 有机化学, 2015, 35(6): 1189-1203.

Cheng Zheng, Zhang Qunfeng, Xu Xiaoliang, Li Xiaonian. Research Progress of Catalytic Synthesis of Benzimidazole Derivatives[J]. Chin. J. Org. Chem., 2015, 35(6): 1189-1203.

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参考文献

[1] Denny, W. A.; Rewcastle, G. W.; Baguley, B. C. J. Med. Chem. 1990, 33, 814.
[2] Huang, S. T.; Hsei, I. J.; Chen, C.; Bioorg. Med. Chem. 2006, 14, 6106.
[3] Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1998, 41, 1252.
[4] Sharma, S.; Gangal, S.; Rauf, A. Eur. J. Med. Chem. 2009, 44, 1751.
[5] Fonseca, T.; Gigantea, B.; Gilchrist, T. L. Tetrahedron 2001, 57, 1793.
[6] Goodwin, K. D.; Lewis, M. A.; Tanious, F. A.; Tidwell, R. R.; David Wilson, W.; Georgiadis, M. M.; Long, E. C. J. Am. Chem. Soc. 2006, 128, 7846.
[7] Zhang, J.; Zhao, W.-M.; Guo, W.-Y.; Wang, Y.; Li, Z.-P. Acta Phys.-Chim. Sin. 2008, 24, 1239 (in Chinese). (张军, 赵卫民, 郭文跃, 王勇, 李中谱, 物理化学学报, 2008, 24, 1239.)
[8] Shen, J.; Yu, D.-S.; Pang, Z.-Z. J. Beijing Univ. Chem. Technol. 2005, 32, 110 (in Chinese). (沈建, 余鼎声, 庞正智, 北京化工大学学报, 2005, 32, 110.)
[9] Isele, K.; Franz, P.; Ambrus, C.; Bernardinelli, G.; Decurtins, S.; Williams, A. F. Inorg. Chem. 2005, 44, 3896.
[10] Miao, Z.-W.; Zhou, W.-H.; Liu, X.-L. Chin. J. Org. Chem. 1999, 19, 537 (in Chinese). (苗志伟, 周卫红, 刘小兰, 有机化学, 1999, 19, 537.)
[11] Raban, M.; Chang, H.; Craine, L. J. Org. Chem. 1985, 50, 2205.
[12] Berrada, M.; Carriere, F.; Abboud. Y. Mater. Chem. 2002, 12, 3551.
[13] Kuroda, N.; Shimoda, R.; Wada, M. Anal. Chim. Acta 2000, 403, 131.
[14] Phillips, M. A. J. Chem. Soc. 1928, 1928, 2393.
[15] Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.
[16] Vanden Eynde, J. J.; Delfosse, F.; Lor, P.; Van Haverbeke, Y. Tetrahedron 1995, 51, 5813.
[17] Lee, K. J.; Janda, K. D. Can. J. Chem. 2001, 79, 1556.
[18] Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293.
[19] Mao, Z.-Z.; Wang, Z.-Y.; Hou, X.-N.; Song, X.-M.; Luo, Y.-F. Chin. J. Org. Chem. 2008, 28, 542 (in Chinese). (毛郑州, 汪朝阳, 侯晓娜, 宋秀美, 罗玉芬, 有机化学, 2008, 28, 542.)
[20] Peng, P.; Xiong, J.-F.; Li, B.; Mo, G.-Z.; Chen, R.-H.; Wang, Z.-Y. Chin. J. Org. Chem. 2013, 33, 1891 (in Chinese). (彭湃, 熊金锋, 李豹, 莫广珍, 陈任宏, 汪朝阳, 有机化学, 2013, 33, 1891.)
[21] 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.)
[22] Sharghi, H.; Asemani, O.; Tabaei, S. M. H. J. Heterocycl. Chem. 2008, 45, 1293.
[23] Han, B.; Jiang, H.-J.; Jia, X.-J.; Gu, X.-H. Appl. Chem. Ind. 2011, 40, 1553 (in Chinese). (韩波, 蒋海金, 贾小维, 顾晓慧, 应用化工, 2011, 40, 1553.)
[24] Fazaeli, R.; Aliyan, H. Appl. Catal. A: Gen. 2009, 353, 74.
[25] Gadekar, L. S.; Arbad, B. R.; Lande, M. K. Chin. Chem. Lett. 2010, 21, 1053.
[26] Ahmad, K. W.; Majid, S. A.; Radha, T. Res. J. Chem. Environ. 2013, 17, 40.
[27] Chari, M. A.; Shobha, D.; Kenawy, E.; Al-Deyab, S. S.; Reddy, B. V. S.; Vinu, A. Tetrahedron Lett. 2010, 51, 5195.
[28] Shingalapur, R. V.; Hosamani, K. M. Catal. Lett. 2010, 137, 63.
[29] Rathod, S. B.; Lande, M. K.; Arbad, B. R. Bull. Korean Chem. Soc. 2010, 31, 2835.
[30] Behbahani, F. K.; Ziaei, P.; Fakhroueian, Z.; Doragi, N. Monatsh. Chem. 2011, 142, 901.
[31] Rekha, M.; Hamza, A.; Venugopal, B. R.; Nagaraju, N. Chin. J. Catal. 2012, 33, 439.
[32] Sharghi, H.; Khalifeh, R.; Mansouri, S. G.; Aberi, M.; Eskandari, M. M. Catal. Lett. 2011, 141, 1845.
[33] Teimouri, A.; Chermahini, A. N.; Salavati, H.; Ghorbanian, L. J. Mol. Catal. A: Chem. 2013, 373, 38.
[34] Inamdar, S. M.; More, V. K.; Mandal, S. K. Tetrahedron Lett. 2013, 54, 579.
[35] Samanta, S.; Das, S.; Biswas, P. J. Org. Chem. 2013, 78, 11184.
[36] Park, S.; Jung, J.; Cho, E. J. Eur. J. Org. Chem. 2014, 4148.
[37] Mungra, D. C.; Patel, M. P.; Patel, R. G. Med. Chem. Res. 2011, 20, 782.
[38] Wang, J.; Li, J.-J.; Chu, H.-T.; Su, L.-Q.; Zhang, Y.-M.; Wei, T.-B. Chem. Res. Appl. 2013, 25, 423 (in Chinese). (王军, 李军舰, 初红涛, 苏立强, 张有明, 魏太保, 化学研究与应用, 2013, 25, 423.)
[39] Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew. Chem. 2008, 120, 9470.
[40] Chen, G. F.; Dong, X. Y. Eur.-J. Chem. 2012, 9, 289.
[41] Jain, R.; Agarwal, D. D.; Sahu, P. K.; Selvam, D. T.; Sharma, Y.; Gupta, R.; Prakash, A. Med. Chem. Res. 2013, 22, 1788.
[42] Srinivasulu, R.; Kumar, K. R.; Satyanarayana, P. V. V. Green Sustainable Chem. 2014, 4, 33.
[43] Bai, G. Y.; Lan, X. W.; Liu, X. F.; Liu, C.; Shi, L. J.; Chen, Q. Z.; Chen, G. F. Green Chem. 2014, 16, 3160.
[44] Niknam, K.; Fatehi-Raviz, A. J. Iran. Chem. Soc. 2007, 4, 438.
[45] Liu, H.; Deng, Y.-J. Spec. Petrochem. 2008, 25, 59 (in Chinese). (刘鸿, 邓勇军, 精细石油化工, 2008, 25, 59).
[46] Ansari, K. F.; Lal, C. Eur. J. Med. Chem. 2009, 44, 4028.
[47] Dey, M.; Deb, K.; Dhar, S. S. Chin. Chem. Lett. 2011, 22, 296
[48] Eren, B.; Erdogan, G. Reac. Kinet., Mech. Catal. 2012, 107, 333.
[49] Bai, C.-B.; Li, J.-J.; Zhang, P.; Zhang, Y.-M.; Wei, T.-B. Chin. J. Synth. Chem. 2012, 20, 359 (in Chinese). (白翠冰, 李军舰, 张鹏, 张有明, 魏太保, 合成化学, 2012, 20, 359.)
[50] Bian, L.; Zeng, X.-C.; He, R.; Luo, C.-L.; Lin, Z.-Q. Chin. J. Org. Chem. 2014, 34, 994 (in Chinese). (卞垒, 曾向潮, 何如, 罗创龙, 林志强, 有机化学, 2014, 34, 994.)
[51] Zhang, Z. H.; Yin, L.; Wang, Y. M. Catal. Commun. 2007, 8, 1126.
[52] Karami, B.; Nikoseresht, S.; Khodabakhshi, S. Chin. J. Catal. 2012, 33, 298.
[53] Karami, B.; Ghashghaee, V.; Khodabakhshi, S. Catal. Commun. 2012, 20, 71.
[54] Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Shoar, R. H.; Bamoharram, F. F. Catal. Commun. 2008, 9, 504.
[55] Sharma, S.; Gangal, S.; Rauf, A. Eur. J. Med. Chem. 2009, 44, 1751.
[56] Khalili, S. B.; Sardarian, A. R. Monatsh. Chem. 2012, 143, 841.
[57] Mayo, M. S.; Yu, X. Q.; Zhou, X. Y.; Feng, X. J.; Yamamoto, Y.; Bao, M. Org. Lett. 2014, 16, 764.
[58] Ren, Y.-M.; Cai, C. Chin. J. Appl. Chem. 2007, 24, 847 (in Chinese). (任一鸣, 蔡春, 应用化学, 2007, 24, 847.)
[59] Blacker, A. J.; Farah, M. M.; Hall, M. I.; Marsden, S. P.; Saidi, O.; Williams, J. M. Org. Lett. 2009, 11, 2039.
[60] Ruiz, V. R.; Corma, A.; Sabater, M. J. Tetrahedron 2010, 66, 730.
[61] Shiraishi, Y.; Sugano, Y.; Tanaka, S.; Hirai, T. Angew. Chem., Int. Ed. 2010, 49, 1656 .
[62] Raghavendra, G. M.; Ramesha, A. B.; Revanna, C. N.; Nandeesh, K. N.; Mantelingu, K.; Rangappa, K. S. Tetrahedron Lett. 2011, 52, 5571.
[63] Yu, J. T.; Xu, J.; Lu, M. Appl. Organomet. Chem. 2013, 27, 606.
[64] Luca, L. D.; Porcheddu, A. Eur. J. Org. Chem. 2011, 5791.
[65] Pizzetti, M.; Luca, E. D.; Petricci, E.; Porcheddu, A.; Taddei, M. Adv. Synth. Catal. 2012, 354, 2453.
[66] Cho, C. S.; Kim, J. U. Bull. Korean Chem. Soc. 2008, 29, 1097.
[67] Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D. Synth. Commun. 2007, 37, 1375.
[68] Wang, J.-K.; Zhang, Y.-J.; Chen, G.-S.; Lu, X.-H. Chem. Reag. 2008, 30, 115 (in Chinese). (王济奎, 张友娟, 陈国松, 陆小华, 化学试剂, 2008, 30, 115.)
[69] Mao, Z.-Z.; Wang, Z.-Y.; Song, X.-M.; Mo, Y.-Q. Chin. J. Org. Chem. 2009, 29, 985 (in Chinese). (毛郑州, 汪朝阳, 宋秀美, 莫阳青, 有机化学, 2009, 29, 985.)
[70] Weires, N. A.; Boster, J; Magolan, J. Eur. J. Org. Chem. 2012, 6508.
[71] Selvam, K.; Swaminathan, M. Tetrahedron Lett. 2011, 52, 3386.
[72] Li, G.; Wang, J.; Yuan, B.; Zhang, D. F.; Lin, Z. Y.; Li, P.; Huang, H. H. Tetrahedron Lett. 2013, 54, 6934.
[73] Tang, L.; Guo, X. F.; Yang, Y.; Zha, Z. G.; Wang, Z. Y. Chem. Commun. 2014, 50, 6145.
[74] Chen, J.; Huang, S. J.; Lin, J.; Su, W. P. Appl. Catal. A: Gen. 2014, 470, 1.
[75] Kim, J.; Kim, J.; Lee, H.; Lee, B. M.; Kim, B. H. Tetrahedron 2011, 67, 8027.
[76] Duan, L. P.; Li, Q.; Wu, N. B.; Xu, D. F.; Zhang, H. B. Chin. Chem. Lett. 2014, 25, 155.
[77] Yu, B.; Zhang, H. Y.; Zhao,Y. F.; Chen, S.; Xu, J. L.; Huang, C. L.; Liu, Z. M. Green Chem. 2013, 15, 95.
[78] Hao, L. D.; Zhao, Y. F.; Yu, B.; Zhang, H. Y.; Xu, H. J.; Liu, Z. M. Green Chem. 2014, 16, 3039.
[79] Zou, B. L.; Yuan, Q. L.; Ma, D. W. Angew. Chem., Int. Ed. 2007, 46, 2598.
[80] Hirano, K.; Biju, A. T.; Glorius, F. J. Org. Chem. 2009, 74, 9570.
[81] Jin, H. W.; Xu, X. L.; Gao, J. R.; Zhong, J. H. Wang, Y. G. Adv. Synth. Catal. 2010, 352, 347.
[82] Kim, Y.; Kumar, M. R.; Park, N.; Heo, Y.; Lee, S. J. Org. Chem. 2011, 76, 9577.
[83] Deng, X. H.; Mani, N. S. Eur. J. Org. Chem.2010, 680.
[84] Jui, N. T.; Buchwald, S. L. Angew. Chem. 2013, 125, 11838.
[85] Hubbard, J. W.; Piegols, A. M.; Soderberg, B. C. G. Tetrahedron. 2007, 63, 7077.
[86] Selvam, K.; Krishnakumar, B.; Velmurugan, R.; Swaminathan, M. Catal. Commun. 2009, 11, 280.
[87] Brasche, G.; Buchwald, S. L. Angew. Chem. 2008, 120, 1958.
[88] Rosen, M. D.; Simon, Z. M.; Tarantino, K. T.; Zhao, L. X.; Rabinowitz, M. H. Tetrahedron Lett. 2009, 50, 1219.
[89] Fu, S. M.; Jiang, H. F.; Deng, Y. F.; Zeng, W. Adv. Synth. Catal. 2011, 353, 2795.
[90] Feng, F.; Xiang, Y.-Z.; Wang, X.-H.; Ma, L.; Lu, C.-S.; Zhang, Q. F.; Xu, X.-L.; Li, X.-N. Sci. China Chem. 2011, 41, 914 (in Chinese). (丰枫, 项益智, 汪小华, 马磊, 卢春山, 张群峰, 许孝良, 李小年, 中国科学: 化学, 2011, 41, 914.)
[91] Li, X.-N.; Ye, J; Zhang, Q. F.; Lu, C.-S.; Feng, F.; Xu, X.-L.; Ma, L. CN 103288743, 2013 [Chem. Abstr. 2013, 159, 516512].