吲哚及其衍生物C2—C3键断裂的反应研究进展
收稿日期: 2022-03-04
修回日期: 2022-03-26
网络出版日期: 2022-08-09
基金资助
国家自然科学基金(21901193); 湖北省大学生创新创业训练(S202110490005)
Research Progress on C2—C3 Bond Cleavage of Indole and Its Derivatives
Received date: 2022-03-04
Revised date: 2022-03-26
Online published: 2022-08-09
Supported by
National Natural Science Foundation of China(21901193); Innovation and Entrepreneurship Training Program for College Students of Hubei Province(S202110490005)
黄泽鑫 , 尹宇强 , 贾丰成 , 吴安心 . 吲哚及其衍生物C2—C3键断裂的反应研究进展[J]. 有机化学, 2022 , 42(7) : 2028 -2044 . DOI: 10.6023/cjoccjoc202203014
Indole building blocks widely exist in many important natural products and drug molecules, and are known as star molecules in bioactive drugs. In view of the outstanding value of indole-based molecules in the field of clinical treatment and drug development, the efficient construction, synthetic transformation and late-stage modification of indole molecules has been an enduring research hotspot in the field of organic synthesis. In recent years, the C2—C3 bond cleavage and reconstruction of indoles have played an important role in the construction of complex molecules and the synthesis of drug molecules, attracting extensive research interests from chemists. This paper systematically summarizes the research progress of C2—C3 bond cleavage/reconstruction reactions of indole and its derivatives in recent years with particular emphasis on reaction strategies, substrate scope and mechanisms.
Key words: indole; indole derivatives; cleavage of C2—C3 bond; reaction mechanism
| [1] | For selected papers, see: (a) Stempel, E.; Gaich, T. Acc. Chem. Res. 2016, 49, 2390. |
| [1] | (b) Zi, W.; Zuo, Z.; Ma, D. Acc. Chem. Res. 2015, 48, 702. |
| [1] | (c) Xu, Z.; Wang, Q.; Zhu, J. Chem. Soc. Rev. 2018, 47, 7882. |
| [2] | (a) Wang, W.; Zhang, M.; Yang, W.; Yang, X. Chin. J. Org. Chem. 2022, 42, 75. (in Chinese) |
| [2] | ( 王弯弯, 张明明, 杨文超, 杨小虎, 有机化学, 2022, 42, 75.) |
| [2] | (b) Shi, Z.; Nie, K.; Liu, C.; Zhang, M.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 327. (in Chinese) |
| [2] | ( 施展, 聂克睿, 刘畅, 张明智, 章维华, 有机化学, 2020, 40, 327.) |
| [3] | For selected examples, see: (a) Robinson, B. Chem. Rev. 1963, 63, 373. |
| [3] | (b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. |
| [3] | (d) Neto, J. S. S.; Zeni, G. Org. Chem. Front. 2020, 7, 155. |
| [4] | (a) Luo, J.; Xu, X.; Zheng, J. Chin. J. Org. Chem. 2018, 38, 363. (in Chinese) |
| [4] | ( 骆钧飞, 徐星, 郑俊良, 有机化学, 2018, 38, 363.) |
| [4] | (b) Wen, J.; Shi, Z. Acc. Chem. Res. 2021, 54, 1723. |
| [4] | (d) Festa, A. A.; Voskressensky, L. G.; Van der Eycken, E. V. Chem. Soc. Rev. 2019, 48, 4401. |
| [4] | (c) Liu, S.; Zhao, F.; Chen, X.; Deng, G.; Huang, H. Adv. Synth. Catal. 2020, 362, 3795. |
| [4] | (d) Huang, G.; Yin, B. Adv. Synth. Catal., 2018, 361, 405. |
| [5] | Shi, Z.; Zhang, B.; Cui, Y.; Jiao, N. Angew. Chem. Int. Ed. 2010, 49, 4036. |
| [6] | Gangadhararao, G.; Uruvakilli, A.; Swamy, K. C. K. Org. Lett. 2014, 16, 6060. |
| [7] | Bakthadoss, M.; Kumar, P. V.; Reddy, T. T.; Sharada, D. S. Org. Biomol. Chem. 2018, 16, 8160. |
| [8] | Lian, X.-L.; Lei, H.; Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2013, 49, 8196. |
| [9] | Feng, Y.; Li, Y.; Cheng, G.; Wang, L.; Cui, X. J. Org. Chem. 2015, 80, 7099. |
| [10] | Yamashita, M.; Nishizono, Y.; Himekawa, S.; Iida, A. Tetrahedron 2016, 72, 4123. |
| [11] | Liu, X. X.; Luo, X. L.; Wu, Z. Y.; Cui, X. F.; Zhou, X. Q.; He, Y. Q.; Huang, G. S. J. Org. Chem. 2017, 82, 2107. |
| [12] | Cao, W. B.; Chu, X. Q.; Zhou, Y.; Yin, L.; Xu, X. P.; Ji, S. J. Chem. Commun. 2017, 53, 6601. |
| [13] | Zhang, L. L.; Cao, W. B.; Xu, X. P.; Ji, S. J. Org. Chem. Front. 2019, 6, 1787. |
| [14] | Cao, W. B.; Liu, B. B.; Xu, X. P.; Ji, S. J. Org. Chem. Front. 2018, 5, 1194. |
| [15] | Ji, X.; Li, D.; Wang, Z.; Tan, M.; Huang, H.; Deng, G. J. Asian J. Org. Chem. 2018, 7, 711. |
| [16] | Xu, M. M.; Cao, W. B.; Xu, X. P.; Ji, S. J. Chem. Commun. 2018, 54, 12602. |
| [17] | Chen, W. L.; Wu, S. Y.; Mo, X. L.; Wei, L. X.; Liang, C.; Mo, D. L. Org. Lett. 2018, 20, 3527. |
| [18] | He, J.; Dong, J.; Su, L.; Wu, S.; Liu, L.; Yin, S. F.; Zhou, Y. Org. Lett. 2020, 22, 2522. |
| [19] | Llpis, N.; Gisbert, P.; Baeza, A. Adv. Synth. Catal. 2021, 363, 3245. |
| [20] | Samineni, R.; Bandi, C. R. C.; Srihari, P.; Mehta, G. Org. Lett. 2016, 18, 6184. |
| [21] | Wang, M.; Yang, Y.; Song, B.; Yin, L.; Yan, S.; Li, Y. Org. Lett. 2019, 22, 155. |
| [22] | Klare, H. F. T.; Goldberg, A. F. G.; Duquette, D. C.; Stoltz, B. M. Org. Lett. 2017, 19, 988. |
| [23] | Holzschneider, K.; Mohr, F.; Kirsch, S. F. Org. Lett. 2018, 20, 7066. |
| [24] | Ubale, A. S.; Shaikh, M. A.; Gnanaprakasam, B. J. Org. Chem. 2021, 86, 9621. |
| [25] | Miao, C. B.; Zeng, Y. M.; Shi, T.; Liu, R.; Wei, P. F.; Sun, X. Q.; Yang, H. T. J. Org. Chem. 2016, 81, 43. |
| [26] | Shao, Y.; Zeng, Y. M.; Ji, J. Y.; Sun, X. Q.; Yang, H. T.; Miao, C. B. J. Org. Chem. 2016, 81, 12443. |
| [27] | He, Y.; Wang, H.; Xu, L.; Li, D. Y.; Ge, J. H.; Feng, D. F.; Feng, W.; Zou, G.; Liu, P. N. Org. Lett. 2021, 24, 121. |
| [28] | Jia, F. C.; Zhou, Z. W.; Xu, C.; Wu, Y. D.; Wu, A. X. Org. Lett. 2016, 18, 2942. |
| [29] | Zhou, Z. W.; Jia, F. C.; Xu, C.; Jiang, S. F.; Wu, Y. D.; Wu, A. X. Chem. Commun. 2017, 53, 1056. |
| [30] | Jiang, S. F.; Xu, C.; Zhou, Z. W.; Zhang, Q.; Wen, X. H.; Jia, F. C.; Wu, A. X. Org. Lett. 2018, 20, 4231. |
| [31] | Li, P. G.; Yan, C.; Zhu, S.; Liu, S. H.; Zou, L. H. Org. Chem. Front. 2018, 5, 3464. |
| [32] | Jia, F. C.; Chen, T. Z.; Hu, X. Q. Org. Chem. Front. 2020, 7, 1635. |
| [33] | (a) Sun, J.; Tan, Q.; Yang, W.; Liu, B.; Xu, B. Adv. Synth. Catal. 2014, 356, 388. |
| [33] | (b) Liu, M.; Shu, M.; Yao, C.; Yin, G.; Wang, D.; Huang, J. Org. Lett. 2016, 18, 824. |
| [34] | Prakash, R.; Gogoi, S. Adv. Synth. Catal. 2016, 358, 3046. |
| [35] | Wang, L. C.; Du, S.; Chen, Z.; Wu, X. F. Org. Lett. 2020, 22, 5567. |
| [36] | Wu, H.; Ma, N.; Song, M.; Zhang, G. Chin. Chem. Lett. 2020, 31, 1580. |
| [37] | Shi, R. G.; Wang, X. H.; Liu, R.; Yan, C. G. Chem. Commun. 2016, 52, 6280. |
| [38] | Balwe, S. G.; Jeong, Y. T. Org. Chem. Front. 2018, 5, 1628. |
/
| 〈 |
|
〉 |