可见光促进C(3)(杂)芳硫基吲哚化合物的合成研究进展
收稿日期: 2023-08-10
修回日期: 2023-10-10
网络出版日期: 2023-11-08
基金资助
四川省教育科研2021年度重点课题(SCJG21A020); 四川省科技厅支撑计划(2015NZ0033)
Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds
Received date: 2023-08-10
Revised date: 2023-10-10
Online published: 2023-11-08
Supported by
Key Project of Sichuan Provincial Education Science Research in 2021(SCJG21A020); Sichuan Provincial Department of Science and Technology Support Program(2015NZ0033)
梅青刚 , 李清寒 . 可见光促进C(3)(杂)芳硫基吲哚化合物的合成研究进展[J]. 有机化学, 2024 , 44(2) : 398 -408 . DOI: 10.6023/cjoc202308008
The structure of 3-sulfenyl indoles widely exists in many drug molecules and natural product molecules. Its derivatives have extensive biological activities such as antibacterial, antiviral and anti-tumor, and are also important intermediates of organic synthesis and structural units of drug synthesis. Therefore, 3-sulfenyl indole compounds have great application value in the field of medicine. The research of its synthesis method has also become one of the current research hotspots. In this paper, the research progress in the synthesis of 3-sulfenyl indoles compounds in recent years is reviewed, and some reaction mechanisms are also discussed.
Key words: 3-sulfenyl indole; photocatalysis; C—S bond formation; synthesis
| [1] | (a) Jia, Y. S.; Wen, X. Y.; Gong, Y. F.; Wang, X. F. Eur. J. Med. Chem. 2020, 200, 112359. |
| [1] | (b) Kumaria, A.; Singh, R. K. Bioorg. Chem. 2019, 89, 103021. |
| [1] | (c) Han, Y.; Dong, W.; Guo, Q.; Li, X.; Huang, L. Eur. J. Med. Chem. 2020, 203, 112506. |
| [2] | Ragno, R.; Coluccia, A.; Regina, L. G.; Martino, D. G.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 3172. |
| [3] | Unangst, C. P.; Connor, T. D.; Stabler, S. R.; Weikert, J. R.; Carethers, E. M.; Kennedy, A. J.; Thueson, O. D.; Chestnut, C. J.; Adolphson, L. R.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360. |
| [4] | Coluccia, A.; Passacantilli, S.; Famiglini, V.; Sabatino, M.; Patsilinakos, A.; Ragno, R.; Mazzoccoli, C.; Sisinni, L.; Okuno, A.; Takikawa, O.; Silvestri, R.; Regina, L. G. J. Med. Chem. 2016, 59, 9760. |
| [5] | Campbell, J. A.; Bordunov, V.; Broka, C. A.; Browner, M. F.; Kress, J. M.; Mirzadegan, T.; Ramesha, C.; Sanpablo, B. F.; Stabler, R.; Takahara, P.; Villasenor, A.; Walker, K. A. M.; Wang, J. H.; Welch, M.; Weller, P. Bioorg. Med. Chem. Lett. 2004, 14, 4741. |
| [6] | La Regina, G.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; De Martino, G.; Matesanz, R.; Díaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865. |
| [7] | Truong, T. S.; Retailleau, P.; Nguyen, T. B. Asian J. Org. Chem. 2022, 11, e202100751. |
| [8] | Vaidya, A. B.; Paul, T. T.; Talwalkar, S. S.; Mankodi, N. A.; Sheth, U. K. J. Postgrad. Med. 1983, 29, 133. |
| [9] | (a) Flynn, B. L.; Flynn, G. P.; Hamel, E.; Jung, M. K. Bioorg. Med. Chem. Lett. 2001, 11, 2341. |
| [9] | (b) Lett, G. D.; Martino, M. C. E.; Regina, G. L.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947. |
| [10] | Dutta, K.; Majumdar, A. G.; Kushwah, N.; Wadawale, A. P.; Patro, B. S.; Ghosh, S. J. Heterocyclic Chem. 2022, 59, 2165. |
| [11] | Tong, Y. X.; Wang, Z. W.; Liu, B.; Xu, Y. W.; Gao, S.; Tang, X. B.; Zhang, X. H. Chin. J. Org. Chem. 2023, 43, 1310 (in Chinese). |
| [11] | (童宇星, 王子维, 刘奔, 徐耀威, 高颂, 唐向兵, 张兴华, 有机化学. 2023, 43, 1310.) |
| [12] | (a) Holmberg-Douglas, N.; Nicewicz, D. A. Chem. Rev. 2022, 122, 1925. |
| [12] | (b) He, S. Q.; Chen, X. L.; Zeng, F. L.; Lu, P. P.; Peng, Y. Y.; Qu, L. B.; Yu, B. Chin. Chem. Lett. 2020, 31, 1863. |
| [12] | (c) Yu, X. Y.; Chen, J. R.; Xiao, W. J. Chem. Rev. 2021, 121, 506. |
| [12] | (d) Sun, G.; Zuo, M.; Qian, W.; Jiao, J.; Hu, X.; Wang, L. Green Synth. Catal. 2021, 2, 32. |
| [12] | (e) Liu, K. J.; Wang, Z.; Lu, L. H.; Chen, J. Y.; Zeng, F.; Lin, Y. W.; Cao, Z.; Yu, X. Y.; He, W. M. Green Chem. 2021, 23, 496. |
| [12] | (f) Cheung, K. P. S.; Sarkar, S.; Gevorgyan, V. Chem. Rev. 2022, 122, 1543. |
| [12] | (g) Coppola, G. A.; Pillitteri, S.; Van der Eycken, E. V.; You, S. L.; Sharma, U. K. Chem. Soc. Rev. 2022, 51, 2313. |
| [12] | (h) Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; Mao, E.; Millet, A.; Oakley, J. V.; Reed, N. L.; Sakai, H. A.; Seath, C. P.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485. |
| [12] | (i) Wang, P. Z.; Xiao, W. J.; Chen, J. R. Nat. Rev. Chem. 2023, 7, 35. |
| [12] | (j) Li, X.; Jiang, M.; Zuo, J. Z.; Song, X. Y.; Lv, J.; Yang, D. S. Sci. China: Chem. 2023, 66, 791. |
| [12] | (k) Xu, H.; Zhang, J.; Zuo, J. Z.; Wang, F. X.; Lu, J.; Hun, X.; Yang, D. S. Chin. J. Org. Chem. 2022, 42, 4037 (in Chinese). |
| [12] | (徐浩, 张杰, 左峻泽, 王丰晓, 吕健, 混旭, 杨道山, 有机化学. 2022, 42, 4037.) |
| [12] | (l) Yang, D. S.; Yan, Q. L.; Zhu, E. J.; Lv, J.; He, W. M. Chin. Chem. Lett. 2022, 33, 1798. |
| [12] | (m) Gui, C. M.; Zhou, T. Y.; Wang, H. F.; Yan, Q. J.; Wang, W.; Huang, J.; Chen, F. E. Chin. J. Org. Chem. 2023, 43, 2647 (in Chinese). |
| [12] | (归春明, 周潼瑶, 王海峰, 严琼姣, 汪伟, 黄锦, 陈芬儿, 有机化学. 2023, 43, 2647.) |
| [12] | (n) Pu, J. X.; Jia, X. Y.; Han, L. R.; Li, Q. H. Chin. J. Org. Chem. 2023, 43, 2591 (in Chinese). |
| [12] | (普佳霞, 贾小英, 韩丽荣, 李清寒, 有机化学. 2023, 43, 2591.) |
| [13] | (a) Wang, P. Z.; Zhao, Q. Q.; Xiao, W.-J.; Chen, J. R. Green Synth. Catal. 2020, 1, 42. |
| [13] | (b) Yu, X. Y.; Chen, J. R.; Xiao, W. J. Chem. Rev. 2021, 121, 506. |
| [13] | (c) Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; Mao, E.; Millet, A.; Oakley, J. V.; Reed, N. L.; Sakai, H. A.; Seath, C. P.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485. |
| [13] | (d) Xuan, L.; Du, R.; Lei, P.; Zhao, W.; Tan, L.; Ni, C.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Green Chem. 2022, 24, 9475. |
| [13] | (e) Wang, P. Z.; Xiao, W. J.; Chen, J. R. Nat. Rev. Chem. 2023, 7, 35. |
| [13] | (f) Dong, J. H.; Xuan, L. M.; Wang, C.; Zhao, C. X.; Wang, H. F.; Yan, Q. J.; Wang, W.; Chen, F. E. Chin. J. Org. Chem. 2024, 44, 111 (in Chinese). |
| [13] | (董江湖, 宣良明, 王池, 赵晨熙, 王海峰, 严琼姣, 汪伟, 陈芬儿, 有机化学. 2024, 44, 111.) |
| [13] | (g) Yang, X. N.; Guo, H. Y.; Zhou, R. Chin. J. Org. Chem. 2023, 43, 2720 (in Chinese). |
| [13] | (杨晓娜, 郭宏宇, 周荣, 有机化学. 2023, 43, 2720.) |
| [14] | (a) Schultz, D. M.; Yoon, T. P. Scienc. 2014, 343, 985. |
| [14] | (b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. |
| [14] | (c) Skubi, K. L.; Blumand, T. R.; Yoon T. P. ; Chem. Rev. 2016, 116, 10035. |
| [14] | (d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
| [14] | (e) Xuan, J.; Xiao, W. J. Angew. Chem.. Int. Ed. 2012, 51, 6828. |
| [14] | (f) Chen, Y. Y.; Lu, L. Q.; Xiao, W. J. Sci China: Chem. 2019, 62, 24. |
| [14] | (g) Zhou, Q. Q.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Angew. Chem.. Int. Ed. 2019, 58, 1586. |
| [14] | (h) Yu, X. Y.; Chen, J. R.; Xiao, W. J. Chem. Rev. 2021, 121, 506. |
| [14] | (i) Xie, Y.; Xuan, J. Chin. J. Org. Chem. 2022, 42, 4247 (in Chinese). |
| [14] | (谢阳, 宣俊, 有机化学. 2022, 42, 4247.) |
| [14] | (j) Candish, L.; Collins, K. D.; Cook, G. C.; Douglas, J. J.; Gómez- Suárez, A.; Jolit, A.; Keess, S. Chem. Rev. 2022, 122, 2907. |
| [14] | (k) Chen, Z. L.; Xie, Y.; Xuan, J. Eur. J. Org. Chem. 2022, e202201066. |
| [15] | (a) Ghosh, S.; Pyne, P.; Ghosh, A.; Choudhury, S.; Hajra, A. Org. Biomol. Chem. 2023, 21, 1591. |
| [15] | (b) Bell, J. D.; Murphy, J. A. Chem. Soc. Rev. 2021, 50, 9540. |
| [16] | (a) Bagdi, A. K.; Rahman, M.; Bhattacherjee, D.; Zyryanov, G. V.; Ghosh, S.; Chupakhin, O. N.; Hajra, A. Green Chem. 2020, 22, 6632. |
| [16] | (b) Cannalire, R.; Pelliccia, S.; Sancineto, L.; Novellino, E.; Tron, G. C.; Giustiniano, M. Chem. Soc. Rev. 2021, 50, 766. |
| [17] | Chen, M.; Huang, Z. T.; Zheng, Q. Y. Chem. Commun. 2012, 48, 11686. |
| [18] | (a) Liu, Q. P.; Huo, C. D.; Fu, Y.; Du, Z. Y. Org. Biomol. Chem. 2022, 20, 6721. |
| [18] | (b) Victoria Bobo, M.; Kuchta, J. J.; Vannucci, A. K. Org. Biomol. Chem. 2021, 19, 4816. |
| [18] | (c) Varlet, T.; Bouchet, D.; Elslande, E. V.; Masson, G. Chem. Eur. J. 2022, 28, e202201707. |
| [19] | Guo, W.; Tan, W.; Zhao, M. M.; Tao, K. L.; Zheng, L. Y.; Wu, Y. Q.; Chen, D. L.; Fan, X. L. RSC Adv. 2017, 7, 37739. |
| [20] | Rahaman, R.; Das, S.; Barman, P. V. Green Chem. 2018, 20, 141. |
| [21] | (a) Ohkubo, K.; Mizushima, K.; Iwataa, R.; Fukuzumi, S. Chem. Sci. 2011, 2, 715. |
| [21] | (b) Cui, H.; Wei, W.; Yang, D.; Zhang, Y.; Zhao, H.; Wang, L.; Wang, H. Green Chem. 2017, 19, 3520. |
| [21] | (c) Zalesskiy, S. S.; Shlapakov, N. S.; Ananikov, V. P. Chem. Sci. 2016, 7, 6740. |
| [21] | (d) Shi, Q.; Li, P. H.; Zhua, X.; Wang, L. Green Chem. 2016, 18, 4916. |
| [22] | Penteado, F.; Caroline S. Gomes, C. S.; Monzon, L. I.; Perin, G.; Claudio C. Silveira, C. C.; Lenard?o, E. J. Eur. J. Org. Chem. 2020, 14, 2110. |
| [23] | Hazarika, S.; Barman, P. ChemistrySelec. 2020, 5, 11583. |
| [24] | Liu, C. P.; Peng, X. J.; Hu, D.; Shi, F.; Huang, P. P.; Luo, J. J.; Liu, Q.; Liu, L. X. New J. Chem. 2020, 44, 17245. |
| [25] | Huang, Q.; Peng, X. J.; Li, H.; He, H. P.; Liu, L. X. Molecule. 2022, 27, 772. |
| [26] | Rathore, V.; Kumar, S. Green Chem. 2019, 21, 2670. |
| [27] | (a) Saba, S.; Rafique, J.; Franco, M. S.; Schneider, A. R.; Esp?ndola, L.; Silva, D. O.; Braga, A. L. Org. Biomol. Chem. 2018, 16, 880. |
| [27] | (b) Guo, W.; Tan, W.; Zhao, M.; Tao, K.; Zheng, L. Y.; Wu, Y.; Chen, D.; Fan, X. L. RSC Adv. 2017, 7, 37739. |
| [27] | (c) Saima, D. E.; Lavekar, A. G.; Sinha, A. K. Org. Biomol. Chem. 2016, 14, 6111. |
| [28] | (a) Su, C. L.; Acik, M.; Takai, K.; Lu, J.; Hao, S. J.; Zheng, Y.; Wu, P. P.; Bao, Q. L.; Enoki, T.; Chabal, Y. J.; Loh, K. P. Nat. Commun. 2012, 3, 1298. |
| [28] | (b) Lv, G. Q.; Wang, H. L.; Yang, Y. G.; Deng, T. S.; Chen, C. M.; Zhu, Y. L.; Hou, X. L. ACS Catal. 2015, 5, 5636. |
| [29] | (a) Arceo, E.; Jurberg, I. D.; lvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750. |
| [29] | (b) Guo, Q.; Wang, M.; Liu, H.; Wang, R.; Xu, Z. Angew. Chem.. Int. Ed. 2018, 57, 4747. |
| [30] | (a) Cheng, Y. Z.; Feng, Z. J.; Zhang, X.; You, S. L. Chem. Soc. Rev. 2022, 51, 2145. |
| [30] | (b) Crisenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461. |
| [30] | (c) Lima, C. G. S.; Lima, T. M.; Duarte, M.; Jurberg, I. D.; Paix?o, M. W. ACS Catal. 2016, 6, 1389. |
| [31] | Yuan, W. K.; Huang, J.; Xu, X.; Wang, L.; Tang, X. Y. Org. Lett. 2021, 23, 7139. |
| [32] | Ye, L.; Chen, J.; Mao, P.; Zhang, X.; Yan, M. Tetrahedron Lett. 2017, 58, 2743. |
| [33] | Priya, V. R. P.; Mercy, A. A. H.; Natarajan, K.; Nandi, G. C. Synlet. 2023, 10.1055/a-2107-5396. |
| [34] | (a) Kumaraswamy, G.; Raju, R.; Narayanarao, V. RSC Adv. 2015, 5, 22718. |
| [34] | (b) Kumar, A.; Gupta, G.; Srivastava, S. Org. Lett. 2011, 13, 6366. |
| [35] | (a) Saha, S.; Bagdi, A. K. Org. Biomol. Chem. 2022, 20, 3249. |
| [35] | (b) Gao, R. Y.; Zuo, L. L.; Wang, F.; Li, C. Y.; Jiang, H. J.; Li, P. H.; Wang, L. Chin. J. Org. Chem. 2022, 42, 1883 (in Chinese). |
| [35] | (高润烨, 左玲玲, 王芳, 李传莹, 蒋华江, 李品华, 王磊, 有机化学. 2022, 42, 1883.) |
| [36] | Shi, Q.; Li, P. H.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322. |
| [37] | Tambe, S. D.; Rohokale, R. S.; Kshirsagar, U. A. Eur. J. Org. Chem. 2018, 18, 2117. |
| [38] | (a) Ghosh, I.; Marzo, L.; Das, A.; Shaikh, R.; Konig, B. Acc. Chem. Res. 2016, 49, 1566. |
| [38] | (b) Babu, S. S.; Muthuraja, P.; Yadav, P.; Gopinath, P. Adv. Synth. Catal. 2021, 363, 1782. |
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