九元氮杂环化合物合成最新研究进展
收稿日期: 2022-06-21
修回日期: 2022-08-10
网络出版日期: 2022-09-02
基金资助
国家自然科学基金(21871062); 国家自然科学基金(22071035)
Recent Advances on the Synthesis of Nine-Membered N-Heterocycles
Received date: 2022-06-21
Revised date: 2022-08-10
Online published: 2022-09-02
Supported by
National Natural Science Foundation of China(21871062); National Natural Science Foundation of China(22071035)
覃小婷 , 邹宁 , 农彩梅 , 莫冬亮 . 九元氮杂环化合物合成最新研究进展[J]. 有机化学, 2023 , 43(1) : 130 -155 . DOI: 10.6023/cjoc202206035
Nine-membered N-heterocycle scaffolds are widely found in natural products and biologically active molecules. The rigid structure of the medium-sized ring plays important roles in the regulation of their biological and pharmacological activities. Therefore, nine-membered N-heterocycle is one of the most attractive medium-sized ring compounds. Because of the increasing entropy and ring extension of nine-membered ring skeleton, the synthesis of nine-membered N-heterocycles is still difficult; especially the effective control of substituent stereoselectivity for the nine-membered ring is one of the greatest challenging topics This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years.
| [1] | Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. |
| [2] | (a) Molander, G. A. Acc. Chem. Res. 1998, 31, 603. |
| [2] | (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073. |
| [2] | (c) Yet, L. Chem. Rev. 2000, 100, 2963. |
| [2] | (d) Hoveyda, A. H.; Zhugralin, A. R. Nature 2007, 450, 243. |
| [2] | (e) Hussain, A.; Yousuf, S. K.; Mukherjee, D. RSC Adv. 2014, 4, 43241. |
| [2] | (f) Li, L.; Li, Z.-L.; Wang, F.-L.; Guo, Z.; Cheng, Y.-F.; Wang, N.; Dong, X.-W.; Fang, C.; Liu, J.; Hou, C.; Tan, B.; Liu, X.-Y Nat. Commun. 2016, 7, 13852. |
| [2] | (g) Li, L.; Li, Z.-L.; Gu, Q.-S.; Wang, N.; Liu, X.-Y. Sci. Adv. 2017, 3, e1701487. |
| [3] | (a) Feng, T.; Cai, X.-H.; Li, Y.; Wang, Y.-Y.; Liu, Y.-P.; Xie, M.-J.; Luo, X.-D. Org. Lett. 2009, 11, 4834. |
| [3] | (b) Beniddir, M. A.; Martin, M.-T.; Dau, M.-E. T. H.; Grellier, P.; Rasoanaivo, P.; Guéritte, F.; Litaudon, M. Org. Lett. 2012, 14, 4162. |
| [3] | (c) Nge, C.-E.; Gan, C.-Y.; Low, Y.-Y.; Thomas, N. F.; Kam, T.-S. Org. Lett. 2013, 15, 4774. |
| [3] | (d) Pan, G.; Williams, R. M. J. Org. Chem. 2012, 77, 4801. |
| [3] | (e) Awakawa, T.; Abe, I. Org. Biomol. Chem. 2018, 16, 4746. |
| [4] | Ryu, M.-J.; Baek, E.-K.; Kim, S.; Seong, C. N.; Yang, I.; Lim, K.-M.; Nam, S.-J. Biomol. Ther. (Seoul) 2021, 29, 98. |
| [5] | Bennasar, M.-L.; Solé, D.; Zulaica, E.; Alonso, S. Org. Lett. 2011, 13, 2042. |
| [6] | Lancefield, C. S.; Zhou, L.; Lébl, T.; Slawin, A. M. Z.; Westwood, N. J. Org. Lett. 2012, 14, 6166. |
| [7] | Pan, G.; Williams, R. M. J. Org. Chem. 2012, 77, 4801. |
| [8] | Magné, V.; Lorton, C.; Marinetti, A.; Guinchard, X.; Voituriez, A. Org. Lett. 2017, 19, 4794. |
| [9] | (a) Zhao, F.-W.; Sun, Q.-Y.; Yang, F.-M.; Hu, G.-W.; Luo, J.-F.; Tang, G.-H.; Wang, Y.-H.; Long, C.-L. Org. Lett. 2010, 12, 3922. |
| [9] | (b) Liang, Y.-Y.; Lu, S.-C.; Gong, Y.-L.; Xu, S. Molecules 2020, 25, 4211. |
| [10] | Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545. |
| [10] | (b) Majumdar, K. C.; Chattopadhyay, B. Synlett 2008, 979. |
| [11] | (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. |
| [11] | (b) Bauer, R. A.; Wenderski, T. A.; Tan, D. S. Nat. Chem. Biol. 2013, 9, 21. |
| [12] | (a) Vo, C.-V. T.; Luescher, M. U.; Bode, J. W. Nat. Chem. 2014, 6, 310. |
| [12] | (b) Jiang, Y.; Ding, L.; Zheng, C.; You, S.-L. Science 2021, 371, 380. |
| [12] | (c) Zhang, Q.-L.; Xiong, Q.; Li, M.-M.; Xiong, W.; Shi, B.; Lan, Y.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2020, 59, 14096. |
| [13] | Li, R.; Xu, X.; Ye, M. Chin. J. Org. Chem. 2020, 40, 3196. (in Chinese) |
| [13] | (李然, 徐学涛, 叶萌春, 有机化学, 2020, 40, 3196.) |
| [14] | Zhang, X.; Lin, L.; Li, J.; Duan, S.; Long, Y.; Li, J. Chin. J. Org. Chem. 2021, 41, 1878. (in Chinese) |
| [14] | (张馨元, 林礼, 李静, 段世妤, 隆宇航, 李加洪, 有机化学, 2021, 41, 1878.) |
| [15] | Prasad, B.; Sreenivas, B. Y.; Sushma, A.; Yellanki, S.; Medistti, R.; Kulkarni, P.; Pal, M. Org. Biomol. Chem. 2014, 12, 2864. |
| [16] | Li, Z.; Kumar, A.; Vachhani, D. D.; Sharma, S. K.; Parmar, V. S.; Eycken, E. V. V. Eur. J. Org. Chem. 2014, 2084. |
| [17] | Kurouchi, H.; Ohwada, T. J. Org. Chem. 2020, 85, 876. |
| [18] | Yang, S.; An, X.-D.; Qiu, B.; Liu, R.-B.; Xiao, J. Org. Lett. 2021, 23, 9100. |
| [19] | Chakraborty, B.; Jana, U. Org. Biomol. Chem. 2021, 19, 10549. |
| [20] | Pacheco, J. C. O.; Opatz, T. J. Org. Chem. 2014, 79, 5182. |
| [21] | Shen, M.-H.; Xu, K.; Sun, C.-H.; Xu, H.-D. Org. Lett. 2015, 17, 5598. |
| [22] | Zhou, B.; Li, L.; Zhu, X.-Q.; Yan, J.-Z.; Guo, Y.-L.; Ye, L.-W. Angew. Chem., Int. Ed. 2017, 56, 4015. |
| [23] | Hall, J. E.; Matlock, J. V.; Ward, J. W.; Gray, K. V.; Clayden, J. Angew. Chem., Int. Ed. 2016, 55, 11153. |
| [24] | Huang, L.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5793. |
| [25] | Guney, T.; Wenderski, T. A.; Boudreau, M. W.; Tan, D. S. Chem. Eur. J. 2018, 24, 13150. |
| [26] | Xu, Z.; Huang, Z.; Li, Y.; Kuniyil, R.; Zhang, C.; Ackermann, L.; Ruan, Z. Green. Chem. 2020, 22, 1099. |
| [27] | Jia, S.; Tian, Y.; Li, X.; Wang, P.; Lan, Y.; Yan, H. Angew. Chem., Int. Ed. 2022, 61, e202206501. |
| [28] | Teng, H.-L.; Yao, L.; Wang, C.-J. J. Am. Chem. Soc. 2014, 136, 4075. |
| [29] | Liu, H.; Wu, Y.; Zhao, Y.; Li, Z.; Zhang, L.; Yang, W.; Jiang, H.; Jing, C.; Yu, H.; Wang, B.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2014, 136, 2625. |
| [30] | Li, Q.-H.; Wei, L.; Wang, C.-J. J. Am. Chem. Soc. 2014, 136, 8685. |
| [31] | He, Z.-L.; Sheong, F. K.; Li, Q.H.; Lin, Z.; Wang, C.-J. Org. Lett. 2015, 17, 1365. |
| [32] | Wu, Y.; Liu, H.; Zhang, L.; Sun, Z.; Xiao, Y.; Huang, J.; Wang, M.; Guo, H. RSC Adv. 2016, 6, 73547. |
| [33] | Yang, L.-C.; Rong, Z.-Q.; Wang, Y.-N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem., Int. Ed. 2017, 56, 2927. |
| [34] | Rong, Z.-Q.; Yang, L.-C.; Liu, S.; Yu, Z.; Wang, Y.-N.; Tan, Z. Y.; Huang, R.-Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304. |
| [35] | Wang, Y.-N.; Yang, L.-C.; Rong, Z.-Q.; Liu, T.-L.; Liu, R.; Zhao, Y. Angew. Chem., Int. Ed. 2018, 57, 1596. |
| [36] | Das, P.; Gondo, S.; Nagender, P. Uno, H.; Tokunaga, E.; Shibata, N. Chem. Sci. 2018, 9, 3276. |
| [37] | Uno, H.; Punna, N.; Tokunaga, E.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2020, 59, 8187. |
| [38] | Uno, H.; Kawai, K.; Shiro, M.; Shibata, N. ACS Catal. 2020, 10, 14117. |
| [39] | Yang, G.; Ke, Y.-M.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 60, 12775. |
| [40] | Liu, Y.; He, Y.; Liu, Y.; Wei, K.; Guo, W. Org. Chem. Front. 2021, 8, 7004. |
| [41] | Lee, K. R.; Ahn, S.; Lee, S.-G. Org. Lett. 2021, 23, 3735. |
| [42] | Li, K.; Yang, S.; Zheng, B.; Wang, W.; Wu, Y.; Li, J.; Guo, H. Chem. Commun. 2022, 58, 6646. |
| [43] | Xie, X.; Yuan, D.; Ma, B.; Jin, J.; Wang, E.; Zhou, W.; Hu, Y.; Hu, L.; Wang, J. Adv. Synth. Catal. 2022, 364, 1168. |
| [44] | Zou, N.; Jiao, J.-W.; Feng, Y.; Chen, C.-H.; Liang, C.; Su, G.-F.; Mo, D.-L. Adv. Synth. Catal. 2017, 359, 3545. |
| [45] | Ma, X.-P.; Li, L.-G.; Zhao, H.-P.; Du, M.; Liang, C.; Mo, D.-L. Org. Lett. 2018, 20, 4571. |
| [46] | Zou, N.; Jiao, J.-W.; Feng, Y.; Pan, C.-X.; Liang, C.; Su, G.-F.; Mo, D.-L. Org. Lett. 2019, 21, 481. |
| [47] | Ma, X.-P.; Nong, C.-M.; Zhao, J.; Lu, X.; Liang, C.; Mo, D.-L. Adv. Synth. Catal. 2020, 362, 478. |
| [48] | Ma, X.-P.; Nong, C.-M.; Liang, Y.-F.; Xu, P.-P.; Guo, X.-Y.; Liang, C.; Pan, C.-X.; Su, G.-F.; Mo, D.-L. Green. Chem. 2020, 22, 3827. |
| [49] | Qin, X.-T.; Zou, N.; Cheng, X.-L.; Liang, C.; Mo, D.-L. Adv. Synth. Catal. 2022, 364, 500. |
| [50] | Gharpure, S. J.; Nanda, S. K.; Fartade, D. J. Org. Biomol. Chem. 2019, 17, 8806. |
| [51] | Chinthapally, K.; Massaro, N. P.; Ton, S.; Gardner, E. D.; Sharma, I. Tetrahedron Lett. 2019, 60, 151253. |
| [52] | Pospech, J.; Ferraccioli, R.; Neumann, H.; Beller, M. Chem. Asian J. 2015, 10, 2624. |
| [53] | Okuma, K.; Kinoshita, H.; Nagahora, N.; Shioji, K. Eur. J. Org. Chem. 2016, 2264. |
| [54] | Torre, A. F.; Rivera, D. G.; Concepción, O.; Echemendia, R.; Correa, A. G.; Paix?o, M. W. J. Org. Chem. 2016, 81, 803. |
| [55] | Yang, W.; Dong, J.; Wang, J.; Xu, X. Org. Lett. 2017, 19, 616. |
| [56] | Cao, J.; Yang, F.; Sun, J.; Huang, Y.; Yan, C.-G. J. Org. Chem. 2019, 84, 622. |
| [57] | Srinivasulu, V.; Schilf, P.; Ibrahim, S.; Shehadi, I. A.; Malik, O. G.; Sieburth, S.; Khanfar, M. A.; Hamad, M.; Abu-Yousef, I. A.; Majdalawieh, A. F.; Al-Tel, T.-H. J. Org. Chem. 2020, 85, 10695. |
| [58] | (a) Baud, L. G.; Manning, M. A.; Arkless, H. L.; Stephens, T. C.; Unsworth, W. P. Chem.-Eur. J. 2017, 23, 2225. |
| [58] | (b) Kitsiou, C.; Hindes, J. J.; Anson, P. I.; Jackson, P.; Wilson, T. C.; Daly, E. K.; Felstead, H. R.; Heanshaw, P.; Unsworth, W. P. Angew. Chem., Int. Ed. 2015, 54, 15794. |
| [59] | Wang, N.; Gu, Q.-S.; Li, Z.-L.; Li, Z.; Guo, Y.-L.; Guo, Z.; Liu, X.-Y. Angew. Chem., Int. Ed. 2018, 57, 14225. |
| [60] | Li, W.; Wang, Y.; Qi, H.; Shi, R.; Li, J.; Chen, S.; Xu, X.-M.; Wang, W.-L. Org. Biomol. Chem. 2021, 19, 8086. |
| [61] | Nathel, N. F. F.; Shah, T. K.; Bronner, S. M.; Garg, N. K. Chem. Sci. 2014, 5, 2184. |
| [62] | Leger, P. R.; Murphy, R. A.; Pushkarskaya, E.; Sarpong, R. Chem. Eur. J. 2015, 21, 4377. |
| [63] | Haynes-Smith, J.; Diaz, I.; Billingsley, K. L. Org. Lett. 2016, 18, 2008. |
| [64] | Magné, V.; Lorton, C.; Marinetti, A.; Guinchard, X.; Voituriez, A. Org. Lett. 2017, 19, 4794. |
| [65] | Chen, C.-M.; Shiao, H.-Y.; Uang, B.-J.; Hsieh, H.-P. Angew. Chem., Int. Ed. 2018, 57, 15572. |
| [66] | Shiomi, S.; Wilailak, K.; Soutome, W.; Takayama, H.; Kitajima, M.; Ishikawa, H. J. Org. Chem. 2022, 87, 3730. |
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