Chinese Journal of Organic Chemistry >
Recent Progress in Synthesis of Polysubstituted Imidazoles by Cyclization Reaction
Received date: 2021-07-05
Revised date: 2021-08-21
Online published: 2021-09-03
Supported by
Scientific Research Foundation of Shaanxi Provincial Key Laboratory(19JS006); Baoji University of Arts and Sciences(ZK2018057)
Imidazoles are a class of very important 5-memeric nitrogen-containing heterocyclic compounds, which have a wide range of applications in organic synthetic chemistry. They are widely found in natural products, applied drugs, materials and other fields, and are also a class of important organic synthesis intermediates. Therefore, the synthetic method of imidazole has attracted much attention. The recent progress in the synthesis of polysubstituted imidazoles by cyclization reaction is summarized. These methods and research progress of the synthesis of imidazoles from oxime esters, 2H-azacyclopropenes, ketones, 2-aminopyridines, azides, triazoles, alkynes, isothiocyanates, aromatic amines, amidines and nitriles are reviewed. Finally, the prospects of the reaction with this reagent are also proposed.
Key words: imidazole; cyclization; synthesis; research process
Mina Zhao , Zimo Yang , Desuo Yang . Recent Progress in Synthesis of Polysubstituted Imidazoles by Cyclization Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 111 -128 . DOI: 10.6023/cjoc202107014
| [1] | (a) Roue, M.; Domart-Coulon, I.; Ereskovsky, A.; Djediat, C.; Perez, T.; Bourguet-Kondracki, M.-L. J. Nat. Prod. 2010, 73, 1277. |
| [1] | (b) Zhang, L.; Peng, X.-M.; Damu, G. L. V.; Geng, R.-X.; Zhou, C.-H. Med. Res. Rev. 2014, 34, 340. |
| [2] | (a) Tang, W.-Z.; Yang, Z.-Z.; Wu, W.; Tang, J.; Sun, F.; Wang, S.-P.; Cheng, C.-W.; Yang, F.; Lin, H.-W. J. Nat. Prod. 2018, 81, 894. |
| [2] | (b) Zhao, K.; Yu, F.; Liu, W.; Huang, Y.; Said, A. A.; Li, Y.; Zhang, Q. J. Org. Chem. 2020, 85, 101. |
| [2] | (c) Qiu, Z.-P.; Tan, J.-H.; Cai, N.; Wang, K.; Ji, S.-M.; Huo, Y.-P. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese) |
| [2] | (邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.) |
| [3] | Rohrig, U. F.; Majjigapu, S. R.; Chambon, M.; Bron, S.; Pilotte, L.; Colau, D.; Van den Eynde, B. J.; Turcatti, G.; Vogel, P.; Zoete, V.; Michielin, O. Eur. J. Med. Chem. 2014, 84, 284. |
| [4] | Perchellet, E. M.; Perchellet, J.-P.; Baures, P. W. J. Med. Chem. 2005, 48, 5955. |
| [5] | Atwell, G. J.; Fan, J.-Y.; Tan, K.; Denny, W. A. J. Med. Chem. 1998, 41, 4744. |
| [6] | Choi, J. Y.; Plummer, M. S.; Starr, J.; Desbonnet, C. R.; Soutter, H.; Chang, J.; Richard Miller, J.; Dillman, K.; Miller, A. A.; Roush, W. R. J. Med. Chem. 2012, 55, 852. |
| [7] | Vlahakis, J. Z.; Lazar, C.; Crandall, I. E.; Szarek, W. A. Bioorg. Med. Chem. 2010, 18, 6184. |
| [8] | Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Richard Keys, J.; Land vatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. Nature 1994, 372, 739. |
| [9] | Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740. |
| [10] | Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. |
| [11] | Mao, P.; Yang, L.-R.; Xiao, Y.-M.; Yuan, J.-W.; Mai, W.-P.; Gao, J.; Zhang, X.-C. Chin. J. Org. Chem. 2019, 39, 443. (in Chinese) |
| [11] | (毛璞, 杨亮茹, 肖咏梅, 袁金伟, 买文鹏, 高杰, 张心持, 有机化学, 2019, 39, 443.) |
| [12] | Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Chem. Rev. 2009, 109, 3859. |
| [13] | Radziszewski, B. Ber. Dtsch. Chem. Ges. 1882, 15, 1493. |
| [14] | Zhao, X.-Y.; Ding, Y.-Y.; Lü, Y.-T.; Kang, C.-M. Chin. J. Org. Chem. 2019, 39, 1304. (in Chinese) |
| [14] | (赵鑫雨, 丁扬扬, 吕英涛, 康从民, 有机化学, 2019, 39, 1304.) |
| [15] | Yang, K.; Yao, C.; Gao, J.-J.; Chen, S.-H.; Zheng, X.-J.; Deng, L.-X.; Zhang, Y.-N.; Liu, M.-J.; Wang, Z.-Y. Chin. J. Org. Chem. 2020, 40, 4168. (in Chinese) |
| [15] | (杨凯, 姚辰, 高娟娟, 陈思鸿, 郑雪洁, 邓璐璇, 张毓娜, 刘美娟, 汪朝阳, 有机化学, 2020, 40, 4168.) |
| [16] | Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 3338. (in Chinese) |
| [16] | (徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, 3338.) |
| [17] | Huang, H.; Ji, X.; Tang, X.; Zhang, M.; Li, X.; Jiang, H. Org. Lett. 2013, 15, 6254. |
| [18] | Zhu, Z.; Tang, X.; Li, J.; Li, X.; Wu, W.; Deng, G.; Jiang, H. Org. Lett. 2017, 19, 1370. |
| [19] | Qu, Z.; Zhang, F.; Deng, G.-J.; Huang, H. Org. Lett. 2019, 21, 8239. |
| [20] | Li, G.; He, R.; Liu, Q.; Wang, Z.; Liu, Y.; Wang, Q. J. Org. Chem. 2019, 84, 8646. |
| [21] | Shi, S.; Xu, K.; Jiang, C.; Ding, Z. J. Org. Chem. 2018, 83, 14791. |
| [22] | Angyal, A.; Demjen, A.; Wolfling, J.; Puskas, L. G.; Kanizsai, I. J. Org. Chem. 2020, 85, 3587. |
| [23] | Vuillermet, F.; Bourret, J.; Pelletier, G. J. Org. Chem. 2021, 86, 388. |
| [24] | Miao, C.; Hou, Q.; Wen, Y.; Han, F.; Li, Z.; Yang, L.; Xia, C.-G. ACS Sustainable Chem. Eng. 2019, 7, 12008. |
| [25] | Pan, Z.; Song, C.; Zhou, W.; Cui, D.-M.; Zhang, C. New J. Chem. 2020, 44, 6182. |
| [26] | Adhikary, S.; Majumder, L.; Pakrashy, S.; Srinath, R.; Mukherjee, K.; Mandal, C.; Banerji, B. ACS Omega 2020, 5, 14394. |
| [27] | Jayram, J.; Jeena, V. Green Chem. 2017, 19, 5841. |
| [28] | Jayram, J.; Jeena, V. RSC Adv. 2018, 8, 37557. |
| [29] | Huang, H.; Ji, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2013, 355, 170. |
| [30] | Chen, X.; Wang, Z.; Huang, H.; Deng, G.-J. Adv. Synth. Catal. 2018, 360, 4017. |
| [31] | Toledo, I.; Grigolo, T. A.; Bennett, J. M.; Elkins, J. M.; Pilli, R. A. J. Org. Chem. 2019, 84, 14187. |
| [32] | Geng, X.; Wang, C.; Huang, C.; Bao, Y.; Zhao, P.; Zhou, Y.; Wu, Y.-D.; Feng, L.-L.; Wu, A.-X. Org. Lett. 2020, 22, 140. |
| [33] | Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416. |
| [34] | Salfeena, C. T. F.; Jalaja, R.; Davis, R.; Suresh, E.; Somappa, S. B. ACS Omega 2018, 3, 8074. |
| [35] | Bhagat, S. B.; Telvekar, V. N. Tetrahedron Lett. 2017, 58, 3662. |
| [36] | Tan, J.; Ni, P.; Huang, H.; Deng, G.-J. Org. Biomol. Chem. 2018, 16, 4227. |
| [37] | Roslan, I. I.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. Catal. Sci. Technol. 2019, 9, 1528. |
| [38] | Reddy, N. N. K.; Rao, S. N.; Ravi, C.; Adimurthy, S. ACS Omega 2017, 2, 5235. |
| [39] | Xiong, J.; Wei, X.; Liu, Z.-M.; Ding, M.-W. J. Org. Chem. 2017, 82, 13735. |
| [40] | Reddy, C. N.; Sathish, M.; Adhikary, S.; Nanubolu, J. B.; Alarifi, A.; Maurya, R. A.; Kamal, A. Org. Biomol. Chem. 2017, 15, 2730. |
| [41] | Necardo, C.; Alfano, A. I.; Grosso, E. D.; Pelliccia, S.; Galli, U.; Novellino, E.; Meneghetti, F.; Giustiniano, M.; Tron, G. C. J. Org. Chem. 2019, 84, 16299. |
| [42] | Man, L.; Copley, R. C. B.; Handlon, A. Org. Biomol. Chem. 2019, 17, 6566. |
| [43] | Zhu, Z.; Lin, H.; Liang, B.; Huang, J.; Liang, W.; Chen, L.; Huang, Y.; Chen, X.; Li, Y. Chem. Commun. 2020, 56, 5621. |
| [44] | Motornov, V.; Markos, A.; Beier, P. Chem. Commun. 2018, 54, 3258. |
| [45] | Arepally, S.; Babu, V. N.; Bakthadoss, M.; Sharada, D. S. Org. Lett. 2017, 19, 5014. |
| [46] | Zhao, Y.; Hu, Y.; Li, X.; Wan, B. Org. Biomol. Chem. 2017, 15, 3413. |
| [47] | Li, X.; Wang, T.; Lu, Y.-J.; Ji, S.; Huo, Y.; Liu, B. Org. Biomol. Chem. 2018, 16, 7143. |
| [48] | He, Q.-X.; Liang, Y.-F.; Xu, C.; Yao, X.-K.; Cao, H.; Yao, H.-G. ACS Comb. Sci. 2019, 21, 149. |
| [49] | Tian, X.; Song, L.; Rudolph, M.; Wang, Q.; Song, X.; Rominger, F.; Hashmi, A. S. K. Org. Lett. 2019, 21, 1598. |
| [50] | Wang, Q.; Chen, X.; Wang, X.-G.; Liu, H.-C.; Liang, Y.-M. Org. Lett. 2019, 21, 9874. |
| [51] | Geng, X.; Liu, S.; Wang, W.; Qu, J.; Wang, B. J. Org. Chem. 2020, 85, 12635. |
| [52] | Li, L.; Luo, Q.; Cui, H.; Li, R.; Zhang, J.; Peng, T. ChemCatChem 2018, 10, 1607. |
| [53] | Senadi, G. C.; Kudale, V. S.; Wang, J.-J. Green Chem. 2019, 21, 979. |
| [54] | Das, S.; Mallick, S.; Sarkar, S. D. J. Org. Chem. 2019, 84, 12111. |
| [55] | Raja, D.; Philips, A.; Palani, P.; Lin, W.-Y.; Devikala, S.; Senadi, G. C. J. Org. Chem. 2020, 85, 11531. |
| [56] | Lin, M.; Wu, F.; Liu, T.-H.; Chen, Z.-T.; Xu, X.-Z.; Ke, F. Chin. J. Org. Chem. 2020, 40, 2563. (in Chinese) |
| [56] | (林媚, 吴凡, 刘天惠, 陈志涛, 许秀枝, 柯方, 有机化学, 2020, 40, 2563.) |
| [57] | Zhao, H.-B.; Hou, Z.-W.; Liu, Z.-J.; Zhou, Z.-F.; Song, J.; Xu, H.-C. Angew. Chem., Int. Ed. 2017, 56, 587. |
| [58] | Wang, J.; Zhang, F.-D.; Tang, D.; Wu, P.; Zhang, X.-G.; Chen, B.-H. RSC Adv. 2017, 7, 24594. |
| [59] | Li, M.; Li, W.; Lin, C.-D.; Wang, J.-H.; Wen, L.-R. J. Org. Chem. 2019, 84, 6904. |
| [60] | Wang, C.; Jiang, H.; Chen, W.; Dong, J.; Chen, Z.; Cao, H. Org. Biomol. Chem. 2017, 15, 6463. |
| [61] | Wang, C.; Wang, E.; Chen, W.; Zhang, L.; Zhan, H.; Wu, Y.; Cao, H. J. Org. Chem. 2017, 82, 9144. |
| [62] | Wang, C.; Lai, J.; Chen, C.; Li, X.; Cao, H. J. Org. Chem. 2017, 82, 13740. |
| [63] | Wang, C.; Yu, Y.; Su, Z.; Li, X.; Cao, H. Org. Lett. 2019, 21, 4420. |
| [64] | Liu, W.; Zhang, Y.; He, J.; Yu, Y.; Yuan, J.; Ye, X.; Zhang, Z.; Xue, L.; Cao, H. J. Org. Chem. 2019, 84, 11348. |
| [65] | Liu, W.; He, J.; Liu, X.; Yu, Y.; Pei, Y.; Zhu, B.; Cao, H. J. Org. Chem. 2020, 85, 14954. |
| [66] | Mauro, G. D.; Maryasin, B.; Kaiser, D.; Shaaban, S.; Gonzalez, L.; Maulide, N. Org. Lett. 2017, 19, 3815. |
| [67] | Xie, J.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2017, 19, 6056. |
| [68] | Ma, H.; Zhang, X.; Chen, L.; Yu, W. J. Org. Chem. 2017, 82, 11841. |
| [69] | Xia, B.; Chen, W.; Zhao, Q.; Yu, W.; Chang, J. Org. Lett. 2019, 21, 2583. |
| [70] | Xu, K.; Yang, R.; Yang, S.; Jiang, C.; Ding, Z. Org. Biomol. Chem. 2019, 17, 8977. |
| [71] | Wang, W.; Zhang, S.; Shi, G.; Chen, Z. Org. Biomol. Chem. 2021, 19, 6682. |
| [72] | Yu, H.; Xiao, L.; Yang, X.; Shao, L. Chem. Commun. 2017, 53, 9745. |
| [73] | Das, U. K.; Shimon, L. J. W.; Milstein, D. Chem. Commun. 2017, 53, 13133. |
| [74] | Huang, X.; Cong, X.; Mi, P.; Bi, X. Chem. Commun. 2017, 53, 3858. |
| [75] | Yu, Y.; Zhang, Y.; Wang, Z.; Liang, Y.-X.; Zhao, Y.-L. Org. Chem. Front. 2019, 6, 3657. |
| [76] | Cai, J.; Bai, H.; Wang, Y.; Xu, X.; Xie, H.; Liu, J. Chem. Commun. 2019, 55, 3821. |
| [77] | Li, Q.-Q.; Ochiai, K.; Lee, C.-A.; Ito, S. Org. Lett. 2020, 22, 6132. |
| [78] | Wang, Y.; Zhou, Y.; Song, Q. Chem. Commun. 2020, 56, 6106. |
/
| 〈 |
|
〉 |