Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 495-506.DOI: 10.6023/cjoc201310012 Previous Articles Next Articles
朱观明, 杨柳阳, 崔冬梅
收稿日期:2013-10-13
修回日期:2013-11-16
发布日期:2013-11-28
通讯作者:
崔冬梅
E-mail:cuidongmei@zjut.edu.cn
基金资助:浙江省自然科学基金（No. Y4100558）资助项目.
Zhu Guanming, Yang Liuyang, Cui Dongmei
Received:2013-10-13
Revised:2013-11-16
Published:2013-11-28
Supported by:Project supported by the Natural Science Foundation of Zhejiang Province (No. Y4100558).
Share
Zhu Guanming, Yang Liuyang, Cui Dongmei. Advances in the Synthetic Methods of Benzimidazoles[J]. Chin. J. Org. Chem., 2014, 34(3): 495-506.
| [1] Zhan, P.; Chen, X. W.; Li, D. Y.; Fang, Z. J.; De Clercq, E.; Liu, X. Y. Med. Chem. Commun. 2013, 33, S1, E1. [2] Leoni, L. M. Semin. Hematol. 2011, 48, S4. [3] Hranjec, M.; Star?evi?, K.; Paveli?, S. K.; Lu?in, P.; Paveli?, K.; Karminski Zamola, G. Eur. J. Med. Chem. 2011, 46, 2274. [4] (a) Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S.; Hugar, M. H. Eur. J. Med. Chem. 2010, 45, 1753. (b) Jain, P.; Sharma, P. K.; Rajak, H.; Pawar, R. S.; Patil, U. K.; Singour, P. K. Arch. Pharm. Res. 2010, 33, 971. [5] (a) Sharma, M. C.; Kohli, D.; Sharma, S.; Sharma, A. D. Pelagia Res. Lib. 2010, 1, 104. (b) Shah, D. I.; Sharma, M.; Bansal, Y.; Bansal, G.; Singh, M. Eur. J. Med. Chem. 2008, 43, 1808. [6] Achar, K.; Hosamani, K. M.; Seetharamareddy, H. R. Eur. J. Med. Chem. 2010, 45, 2048. [7] Ku?, C.; Ayhan-K?lc?gil, G.; Özbey, S.; Kaynak, F. B.; Kaya, M.; Çoban, T.; Can-Eke, B. Bioorg. Med. Chem. 2008, 16, 4294. [8] Pérez-Villanueva, J.; Santos, R.; Hernández-Campos, A.; Giulianotti, M. A.; Castillo, R.; Medina-Franco, J. L. Med. Chem. Commun. 2011, 2, 44. [9] Meng, J.-P.; Geng, R.-X.; Zhou, C.-H.; Gan, L.-L. Chin. J. New Drugs 2009, 18, 1505 (in Chinese).(孟江平, 耿蓉霞, 周成合, 甘淋玲, 中国新药杂志, 2009, 18, 1505.)[10] Li, Y.; Ma, H.-Q.; Wang, Y.-L. Chin. J. Org. Chem. 2008, 28, 210 (in Chinese).(李焱, 马会强, 王玉炉, 有机化学, 2008, 28, 210.)[11] Chawla, A.; Kaur, G.; Sharma, A. K. Int. J. Pharm. Phytopharmacol. Res. 2012, 2, 148. [12] Panda, S. S.; Malik, R.; Jain, S. C. Curr. Org. Chem. 2012, 16, 1905.[13] 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.) [14] Mao, Z.-Z.; Li, J.-X.; Xue, F.-L.; Chen, R.-H.; Wang, Z.-Y. Chem. Res. Appl. 2012, 24, 497 (in Chinese).(毛郑州, 李建晓, 薛福玲, 陈任宏, 汪朝阳, 化学研究与应用, 2012, 24, 497.)[15] Chawla, A.; Kaur, R.; Goyal, A. J. Chem. Pharm. Res. 2011, 3, 925. [16] 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.)[17] Carvalho, L. C.; Fernandes, E.; Marques, M. M. B. Chem.-Eur. J. 2011, 17, 12544. [18] Mamedov, V. A.; Murtazina, A. M. Russ. Chem. Rev. 2011, 80, 397. [19] (a) Dawood, K. M.; Elwan, N. M.; Farahat, A. A.; Abdel-Wahab, B. F. J. Heterocycl. Chem. 2010, 47, 2437. (b) Dawood, K. M.; Elwan, N. M.; Abdel-Wahab, B. F. ARKIVOC 2011, (i), 111. (c) Dawood, K. M.; Abdel-Wahab, B. F. ARKIVOC 2010, (i), 333. [20] Linschitz, H.; Grellmann, K. H. J. Am. Chem. Soc. 1964, 86, 303. [21] Carvalho, L. C. R.; Fernandes, E.; Marques, M. M. B. Chem.-Eur. J. 2011, 17, 12544. [22] Chebolu, R.; Kommi, D. N.; Kumar, D.; Bollineni, N.; Chakraborti, A. K. J. Org. Chem. 2012, 77, 10158. [23] Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61. [24] Ghorbani Vaghei, R.; Veisi, H. Mol. Diversity 2010, 14, 249. [25] Khosravi, K.; Kazemi, S. Chin. Chem. Lett. 2012, 23, 61. [26] G Smith, J.; Ho, I. Tetrahedron Lett. 1971, 12, 3541. [27] Lin, S. N.; Yang, L. H. Tetrahedron Lett. 2005, 46, 4315. [28] Panda, S. S.; Jain, S. C. Synth. Commun. 2011, 41, 729. [29] Zhang, C.; Zhang, L.-R.; Jiao, N. Green Chem. 2012, 14, 3273. [30] Chen, G.-F.; Shen, H.-D.; Jia, H.-M.; Zhang, L.-Y.; Kang, H.-Y.; Qi, Q.-Q.; Chen, B.-H.; Cao, J.-L. Aust. J. Chem. 2013, 66, 262. [31] Ben Alloum, A.; Bakkas, S.; Soufiaoui, M. Tetrahedron Lett. 1998, 39, 4481. [32] Chang, J. B.; Zhao, K.; Pan, S. F. Tetrahedron Lett. 2002, 43, 951. [33] Beaulieu, P. L.; Haché, B.; von Moos, E. Synthesis 2003, 1683. [34] Wang, H.-S.; Miao, J.-Y.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 615 (in Chinese).(王宏社, 苗建英, 赵立芳, 有机化学, 2005, 25, 615.) [35] (a) Osowska, K.; Miljanic, O. S. J. Am. Chem. Soc. 2011, 133, 724. (b) Lee, I. L.; Li, S.-R.; Chen, K.-F.; Ku, P.-J.; Singh, A. S.; Kuo, H.-T.; Wen, Y.-S.; Chu, C.-W. Eur. J. Org. Chem. 2012, 15, 2906. [36] Sharghi, H.; Hosseini Sarvari, M.; Moeini, F. Can. J. Chem. 2008, 86, 1044. [37] Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835. [38] Chandrachood, P. S.; Garud, D. R.; Gadakari, T. V.; Torane, R. C.; Deshpande, N. R.; Kashalkar, R. V. Acta Chem. Slov. 2011, 58, 367. [39] Sharghi, H.; Aberi, M.; Doroodmand, M. M. Adv. Synth. Catal. 2008, 350, 2380. [40] Singh, M. P.; Sasmal, S.; Lu, W.; Chatterjee, M. N. Synthesis 2000, 1380. [41] Kadish, K. M.; Smith, K. M.; Guilard, R. The Porphyrin Handbook: Inorganic, Organometallic and Coordination Chemistry, Vol. 3, Elsevier, London, 2003. [42] Abdollahi Alibeik, M.; Moosavifard, M. Synth. Commun. 2010, 40, 2686. [43] Fazlinia, A.; Mosslemin, M. H.; Sadoughi, H. J. Korean Chem. Soc. 2010, 54, 579. [44] Chen, G. F.; Dong, X. Y.; Meng, F. Z.; Chen, B. H.; Li, J. T.; Wang, S. X.; Bai, G. Y. Lett. Org. Chem. 2011, 8, 464. [45] Leutbecher, H.; Constantin, M. A.; Mika, S.; Conrad, J.; Beifuss, U. Tetrahedron Lett. 2011, 52, 605. [46] Coppola, G. M. Synth. Commun. 2008, 38, 3500. [47] Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew. Chem., Int. Ed. 2008, 120, 9470. [48] Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Norouzi, L. Monatsh. Chem. 2009, 140, 547. [49] Aliyan, H.; Fazaeli, R.; Fazaeli, N.; Mssah, A. R.; Naghash, H. J.; Alizadeh, M.; Emami, G. Heteroat. Chem. 2009, 20, 202. [50] Chari, M. A.; Shobha, D.; Kenawy, E. R.; Al Deyab, S. S.; Reddy, B.; Vinu, A. Tetrahedron Lett. 2010, 51, 5195. [51] Dhakshinamoorthy, A.; Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2011, 52, 69. [52] Meshram, G. A.; Patil, V. D. Int. J. Chem. Sci. 2010, 8, 119. [53] Adharvana Chari, M.; Shobha, D.; Sasaki, T. Tetrahedron Lett. 2011, 52, 5575. [54] Behbahani, F. K.; Ziaei, P.; Fakhroueian, Z.; Doragi, N. Monatsh. Chem. 2011, 142, 9, 901. [55] Zhu, G. M.; Zhuo, Z. J.; Cui, D. M.; Zhang, C. In Chinese Chemistry Society?The 8th National Organic Chemistry Conference & the 1th Chongqing International Symposium on Organic Chemistry, Chongqing, 2013, p. 389 (in Chinese).(朱观明, 卓子健, 崔冬梅, 张辰, 在中国化学会第八届有机化学会议暨首届重庆有机化学国际研讨会, 重庆, 2013, p. 389.)[56] Han, X. M.; Ma, H. Q.; Wang, Y. L. ARKIVOC 2007, xiii, 150. [57] Chakrabarty, M.; Mukherjee, R.; Karmakar, S.; Harigaya, Y. Monatsh. Chem. 2007, 138, 1279. [58] Mohammadi, A. A.; Azizian, J.; Karimi, N. Heterocycles 2009, 78, 2337. [59] Wang, X. B.; Jian, T. Y.; Ma, X. W.; He, L. Chin. J. Org. Chem. 2012, 32, 2181 (in Chinese).(王湘波, 简腾跃, 马晓伟, 何林, 有机化学, 2012, 32, 2181.) [60] Srinivas, U.; Srinivas, C.; Narender, P.; Rao, V. J.; Palaniappan, S. Catal. Commun. 2007, 8, 107. [61] Sharghi, H.; Asemani, O.; Khalifeh, R. Synth. Commun. 2008, 38, 1128. [62] Saha, D.; Saha, A.; Ranu, B. C. Green Chem. 2009, 11, 733. [63] Rostamizadeh, S.; Aryan, R.; Ghaieni, H. R.; Amani, A. M. J. Heterocycl. Chem. 2009, 40, 74. [64] Lei, M.; Ma, L.; Hu, L. H. Synth. Commun. 2012, 42, 2981. [65] Jadhav, G. R.; Shaikh, M. U.; Kale, R. P.; Gill, C. H. Chin. Chem. Lett. 2009, 20, 535. [66] Bahrami, K.; Khodaei, M. M.; Nejati, A. Green Chem. 2010, 12, 1237. [67] Molander, G. A.; Ajayi, K. Org. Lett. 2012, 14, 4242. [68] (a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. (b) Guillena, G.; Ramon, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611. [69] Bala, M.; Kumar Verma, P.; Sharma, U.; Kumar, N.; Singh, B. Green Chem. 2013, 15, 1687. [70] (a) Shiraishi, Y.; Sugano, Y.; Tanaka, S.; Hirai, T. Angew. Chem., Int. Ed. 2010, 49, 1656. (b) Selvam, K.; Swaminathan, M. Tetrahedron Lett. 2011, 52, 3386. [71] (a) Rope, M.; Isensee, R. W.; Joseph, L. J. Am. Chem. Soc. 1952, 74, 1095. (b) Sandera, G.; Isensee, R. W.; Joseph, L. J. Am. Chem. Soc. 1954, 76, 5173. [72] Clemens, J. J.; Davis, M. D.; Lynch, K. R.; Macdonald, T. L. Bioorg. Med. Chem. Lett. 2004, 14, 4903. [73] Wen, X.; Bakali, J. E.; Deprez-Poulain, R.; Deprez, B. Tetrahedron Lett. 2012, 53, 2440. [74] Thomas, O. D.; Soo, K. J. W. Y.; Peckham, T. J.; Kulkarni, M. P.; Holdcroft, S. J. Am. Chem. Soc. 2012, 134, 10753. [75] Algul, O.; Kaessler, A.; Apcin, Y.; Yilmaz, A.; Jose, J. Molecules 2008, 13, 736. [76] Khattab, M.; Galal, S. A.; Ragab, F. A. F.; Diwani, H. I. E. Res. Chem. Intermed. 2013, 39, 2917. [77] Khalili, S. B.; Sardarian, A. R. Monatsh. Chem. 2012, 143, 841. [78] Bommegowda, Y. K.; Lingaraju, G. S.; Thamas, S.; Vinay Kumar, K. S.; Pradeepa Kumara, C. S.; Rangappa, K. S.; Sadashiva, M. P. Tetrahedron Lett. 2013, 54, 2693. [79] (a) Perry, R. J.; Wilson, B. D. J. Org. Chem. 1993, 58, 7016. (b) She, J.; Jiang, Z.; Wang, Y. Synlett 2009, 2023. [80] VanVliet, D. S.; Gillespie, P.; Scicinski, J. J. Tetrahedron Lett. 2005, 46, 6741. [81] Mamedov, V. A.; Zhukova, N. A.; Beschastnova, T. N.; Zakirova, E. V. I.; Kadyrova, S. F.; Mironova, E. V.; Nikonova, A. G.; Latypov, S. K. Tetrahedron Lett. 2012, 53, 292. [82] Mamedov, V. A.; Murtazina, A. M. Russ. Chem. Rev. 2011, 80, 397. [83] Esser, F.; Ehrengart, P.; Ignatow, H. P. J. Chem. Soc., Perkin Trans. 1 1999, 1153. [84] Makosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20, 282. [85] Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Org. Lett. 2013, 15, 1334. [86] Sadig, J. E. R.; Foster, R.; Wakenhut, F.; Willis, M. C. J. Org. Chem. 2012, 77, 9473. [87] Yu, H.; Liu, Q.; Li, Y.; Ni, C. Tetrahedron Lett. 2012, 53, 5253. [88] Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 120, 1958. [89] Qu, Y. Y.; Pan, L.; Wu, Z. Q.; Zhou, X. G. Tetrahedron 2013, 69, 1717. [90] Peng, J. S.; Ye, M.; Zong, C. J.; Hu, F. Y.; Feng, L. T.; Wang, X. Y.; Wang, Y. F.; Chen, C. X. J. Org. Chem. 2010, 76, 716. [91] Giri, R.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 15860. [92] Liubchak, K.; Nazarenko, K.; Tolmachev, A. Tetrahedron 2012, 68, 2993. [93] Creutz, S. E.; Lotito, K. J.; Fu, G. C.; Peters, J. C. Science 2012, 338, 647. [94] Ziegler, D. T.; Choi, J.; Muêoz-Molina, J. M.; Bissember, A. C.; Peters, J. C.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 13107. [95] (a) Zhang, C.; Zhang, S. Q.; Cai, H. J.; Cui, D. M. Beilstein J. Org. Chem. 2013, 9, 1045. (b) Cui, D. M.; Zheng, Z. L.; Zhang, C. J. Org. Chem. 2009, 74, 1426. (c) Cui, D. M.; Zhuang, D. W.; Chen, Y.; Zhang, C. Beilstein J. Org. Chem. 2011, 7, 860. (d) Cui, D. M.; Yu, K. R.; Zhang, C. Synlett 2009, 1103. [96] (a) Cui, D. M.; Zheng, J. Z.; Yang, L. Y.; Zhang, C. Synlett 2010, 809. (b) Cui, D. M.; Meng, Q.; Zheng, J. Z.; Zhang, C. Chem. Commun. 2009, 1577. [97] Cui, D.-M.; Zhuang, D.-W.; Chen, Y.; Zhang, C. Beilstein J. Org. Chem. 2011, 7, 860. [98] Li, Z.-G.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. |
| [1] | Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136. |
| [2] | Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147. |
| [3] | Mengjia Xiao, Xike Gao. Design, Synthesis and Anti-inflammatory Activity of Azulene Derivatives Containing Benzimidazole Unit [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3246-3256. |
| [4] | Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205. |
| [5] | Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240. |
| [6] | Tiantian Liu, Xinhong Duan. Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3695-3712. |
| [7] | Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783. |
| [8] | Zhiyuan Chen, Mengwei Yang, Jianlin Xu, Yunhe Xu. Regioselective Synthesis of β-Silyl-Substituted Vinylphosphine Oxides via Copper-Catalyzed Protosilylation of Dialkynylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3598-3607. |
| [9] | Xiangkun Meng, Zhengyuan Qi, Lei Yu, Yiyang Zhang. Catalytic System for Poly(lactic acid) Synthesis: Opportunities and Challenges [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 112-119. |
| [10] | Xudong Cui, Xiangkun Meng, Ying Chen, Yonghong Liu, Lei Yu. Preparation of L-Lactide with High Optical Purity via the Zinc-Doped Polypyrrole-Catalyzed Lactic Acid Condensation [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2954-2960. |
| [11] | Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558. |
| [12] | Shouyi Cen, Zhipeng Zhang. Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2574-2581. |
| [13] | Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183. |
| [14] | Runye Gao, Lingling Zuo, Fang Wang, Chuanying Li, Huajiang Jiang, Pinhua Li, Lei Wang. Recent Advances in Controllable Organic Reactions Induced by Visible Light without External Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1883-1903. |
| [15] | Tao Li, Yi Liu, Xue Bai, Zunjun Zhou, Peng Zuo, Miaofeng Ma, Chong-Min Zhong, Ya-Jie Zuo. Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1713-1721. |
| Viewed | ||||||
|
Full text |
|
|||||
|
Abstract |
|
|||||
