N-芳基丙烯酰胺与自由基级联环化合成2-吲哚酮研究进展

doi:10.6023/cjoc202501016

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3691-3700.DOI: 10.6023/cjoc202501016 上一篇下一篇

综述与进展

N-芳基丙烯酰胺与自由基级联环化合成2-吲哚酮研究进展

伍智林^a, 罗伟^a, 丁柔^a^,^b, 辛翠^c^,^*(), 王从洋^d^,^*(), 何卫民^a^,^*()

^a 南华大学化学化工学院湖南衡阳 421001
^b 南京林业大学林木生物质低碳高效利用国家工程研究中心南京 210037
^c 湖南警察学院食药环及毒品检验技术湖南省普通高等学校重点实验室长沙 410138
^d 中国科学院化学研究所中国科学院分子识别与功能重点实验室北京 100190

收稿日期:2025-01-16 修回日期:2025-02-18 发布日期:2025-03-13
基金资助:
湖南省科技创新计划(2022RC4044)

Research Progress on the Synthesis of 2-Oxindoles via Radical Cascade Cyclization of N-Arylacrylamide

Zhilin Wu^a, Wei Luo^a, Rou Ding^a^,^b, Cui Xin^c^,^*(), Congyang Wang^d^,^*(), Wei-Min He^a^,^*()

^a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
^b National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037
^c Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138
^d CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2025-01-16 Revised:2025-02-18 Published:2025-03-13
Contact: * xin-cui@163.com; wangcy@iccas.ac.cn; weiminhe@usc.edu.cn
Supported by:
Science and Technology Innovation Program of Hunan Province(2022RC4044)

文章分享

摘要/Abstract

2-吲哚酮是一类广泛存在于天然活性产物和药物分子中的骨架结构, N-芳基丙烯酰胺自由基级联环化反应是合成此类化合物最有效的方法. 合适的自由基前体可在光、电或热驱动下产生相应的自由基, 从而诱导N-芳基丙烯酰胺发生自由基级联环化反应合成2-吲哚酮. 系统介绍了近年来通过光、电和热驱动引发的自由基产生及其与N-芳基丙烯酰胺级联环化反应合成2-吲哚酮的研究进展.

关键词: 光催化, 电催化, 2-吲哚酮, N-芳基丙烯酰胺

2-Oxindole is a widely present skeletal structure in natural active products and drug molecules, and the radical cascade cyclization of N-arylacrylamide is the most effective method for synthesizing such compounds. Suitable free radical precursors can generate corresponding free radicals under the drive of light, electricity, or heat, thereby inducing a free radical cascade cyclization reaction of N-arylacrylamide to synthesize 2-oxindoles. Herein the research progress on the generation of free radicals induced by light, electricity, and heat in recent years and their application in the cascade cyclization of N-arylacrylamide to synthesize 2-oxindoles are systematically introduced.

Key words: photocatalysis, electrocatalysis, 2-oxindole, N-arylacrylamide

引用此文

伍智林, 罗伟, 丁柔, 辛翠, 王从洋, 何卫民. N-芳基丙烯酰胺与自由基级联环化合成2-吲哚酮研究进展[J]. 有机化学, 2025, 45(10): 3691-3700.

Zhilin Wu, Wei Luo, Rou Ding, Cui Xin, Congyang Wang, Wei-Min He. Research Progress on the Synthesis of 2-Oxindoles via Radical Cascade Cyclization of N-Arylacrylamide[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3691-3700.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 12

图1. 含2-吲哚酮骨架的活性天然产物和生物活性化合物

Figure 1. Examples of 2-oxindole moiety of natural products and bioactive compounds

图式1. 由N-芳基丙烯酰胺合成3-官能化2-吲哚酮的一般机理

Scheme 1. General mechanism of synthesizing 3-functionalized 2-oxindole from N-arylacrylamide

图式2. 铱配合物催化合成2-吲哚酮

Scheme 2. Synthesis of 2-oxindoles catalyzed by iridium complex

图式3. Eosin Y催化合成2-吲哚酮

Scheme 3. Synthesis of 2-oxindoles catalyzed by Eosin Y

图式4. 4CzIPN催化合成2-吲哚酮

Scheme 4. Synthesis of 2-oxindoles catalyzed by 4CzIPN

图式5. N-杂环氮鎓盐催化合成2-吲哚酮

Scheme 5. Synthesis of 2-oxindoles catalyzed by NHN

图式6. 聚合物CC-CMP催化合成2-吲哚酮

Scheme 6. Synthesis of 2-oxindoles catalyzed by CC-CMP

图式7. 无光催化剂参与下合成2-吲哚酮

Scheme 7. Synthesis of 2-oxindoles without photocatalyst

图式8. CTC策略合成2-吲哚酮

Scheme 8. Synthesis of 2-oxindoles using CTC strategy

图式9. 电催化合成2-吲哚酮

Scheme 9. Electrocatalytic synthesis of 2-oxindoles

图式10. 热驱动钯配合物催化合成2-吲哚酮

Scheme 10. Thermally driven synthesis of 2-oxindoles catalyzed by palladium complex

图式11. 氧化剂辅助合成2-吲哚酮

Scheme 11. Oxidant-assisted synthesis of 2-oxindol

参考文献 31

[1]	(a) Du, J.; Wang, X.; Wang, H.; Wei, J.; Huang, X.; Song, J.; Zhang, J. Org. Lett. 2021, 23, 5631.
	(b) Fan, X.; Lei, T.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2019, 21, 4153.
[2]	Muralirajan, K.; Kancherla, R.; Gimnkhan, A.; Rueping, M. Org. Lett. 2021, 23, 6905.
[3]	Li, X.; Zhao, H.; Meng, L.; Dong, J.; Yang, C.; Wei, Z.; Wang, X.; Xu, J.; Fan, B. J. Org. Chem. 2023, 88, 5300.
[4]	Pei, C.; Liu, Y.; Chen, X.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Adv. Synth. Catal. 2023, 365, 860.
[5]	Roy, V. J.; Dagar, N.; Choudhury, S.; Raha Roy, S. J. Org. Chem. 2023, 88, 15374.
[6]	Lu, M.; Zhang, T.; Tan, D.; Chen, C.; Zhang, Y.; Huang, M.; Cai, S. Adv. Synth. Catal. 2019, 361, 4237.
[7]	Yu, W. L.; Luo, Y. C.; Yan, L.; Liu, D.; Wang, Z. Y.; Xu, P. F. Angew. Chem., Int. Ed. 2019, 58, 10941.
[8]	(a) Xian, N.; Yin, J.; Ji, X.; Deng, G.-J.; Huang, H. Org. Lett. 2023, 25, 1161.
	(b) Yan, W.; Qu, Z.; Zhao, F.; Deng, G. J.; Mao, G. J.; Huang, H. Adv. Synth. Catal. 2023, 365, 612.
[9]	Zhang, C.-S.; Fang, C.-Z.; Yi, L.; Zhu, C.; Wang, Z.-X.; Chen, X.-Y.; Rueping, M. Org. Chem. Front. 2024, 11, 673.
[10]	Ou, W.; Zhang, G.; Wu, J.; Su, C. ACS Catal. 2019, 9, 5178.
[11]	Zhou, C.; Wang, R.; Gao, L.; Huang, X.; Zhang, X. ACS Appl. Mater. Interfaces 2022, 14, 30962.
[12]	(a) Hou, J.-C.; Ji, H.-T.; Lu, Y.-H.; Wang, J.-S.; Xu, Y.-D.; Zeng, Y.-Y.; He, W.-M. Chin. Chem. Lett. 2024, 35, 109514.
	(b) Hou, J.-C.; Cai, W.; Ji, H.-T.; Ou, L.-J.; He, W.-M. Chin. Chem. Lett. 2025, 36, 110469.
	(c) Song, H.-Y.; Xiao, F.; Jiang, J.; Wu, C.; Ji, H.-T.; Lu, Y.-H.; Wang, K.-L.; He, W.-M. Chin. Chem. Lett. 2023, 34, 108509.
	(d) Gui, Q.-W.; Teng, F.; Li, Z.-C.; Xiong, Z.-Y.; Jin, X.-F.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1907.
	(e) Ji, H.-T.; Lu, Y.-H.; Liu, Y.-T.; Huang, Y.-L.; Tian, J.-F.; Liu, F.; Zeng, Y.-Y.; Yang, H.-Y.; Zhang, Y.-H.; He, W.-M. Chin. Chem. Lett. 2025, 36, 110568.
[13]	Wu, Z.-L.; Liu, J.-T.; Zhou, R.-W.; Deng, M.-Q.; Li, X.; Ji, H.-T.; He, W.-M. J. Org. Chem. 2024, 89, 12693.
[14]	(a) Ye, Z. P.; Yang, J. S.; Yang, S. J.; Guo, M.; Yuan, C. P.; Ye, Y. Q.; Chen, H. B.; Xiang, H. Y.; Chen, K.; Yang, H. Org Lett 2023, 25, 7062.
	(b) Lu, Y.; Fang, C. Z.; Liu, Q.; Li, B. L.; Wang, Z. X.; Chen, X. Y. Org. Lett. 2021, 23, 5425.
	(c) Cheng, H.; Luo, Y.; Lam, T.-L.; Liu, Y.; Che, C.-M. Org. Chem. Front. 2022, 9, 5962.
	(d) Matsuo, B.; Majhi, J.; Granados, A.; Sharique, M.; Martin, R. T.; Gutierrez, O.; Molander, G. A. Chem. Sci. 2023, 14, 2379.
	(e) Hou, H.; Ou, W.; Su, C. J. Org. Chem. 2024, 89, 4120.
[15]	Zhang, M.-Z.; Yang, X.; Yin, J.-X.; Deng, Y.; Tan, H.-Y.; Bai, Y.-H.; Li, Y.-L.; Wen, J.; Chen, T. Org. Lett. 2024, 26, 3923.
[16]	Bao, L.; Wang, Z.-X.; Chen, X.-Y. Org. Lett. 2022, 24, 8223.
[17]	Ren, Y.-Z.; Fang, C.-Z.; Zhang, B.-B.; He, L.; Tu, Y.-L.; Chen, X.-Y. Org. Lett. 2023, 25, 3585.
[18]	(a) Ruan, Z.; Huang, Z.; Xu, Z.; Mo, G.; Tian, X.; Yu, X.-Y.; Ackermann, L. Org. Lett. 2019, 21, 1237.
	(b) Zhang, Z.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.; Liu, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 762.
	(c) Wang, H.; Xie, Y.; Zhou, Y.; Cen, N.; Chen, W. Chin. Chem. Lett. 2022, 33, 221.
[19]	(a) Wang, X. Y.; Zhong, Y. F.; Mo, Z. Y.; Wu, S. H.; Xu, Y. L.; Tang, H. T.; Pan, Y. M. Adv. Synth. Catal. 2020, 363, 208.
	(b) Cheng, X.; Hasimujiang, B.; Xu, Z.; Cai, H.; Chen, G.; Mo, G.; Ruan, Z. J. Org. Chem. 2021, 86, 16045.
[20]	(a) Chen, C.; Liu, R.-X.; Xiong, F.; Li, Z.-H.; Kang, J.-C.; Ding, T.-M.; Zhang, S.-Y. Chem. Commun. 2022, 58, 9230.
	(b) Dai, Y.; Cui, M.; Li, X.; Chen, H.; Xu, X. New J. Chem. 2023, 47, 5780.
[21]	Lv, Y.; Hou, Z.-W.; Wang, Y.; Li, P.; Wang, L. Org. Biomol. Chem. 2023, 21, 1014.
[22]	Zhou, X.; Wang, J.; Shen, Y.; Ma, D.; Zhao, Y.; Wu, J. J. Org. Chem. 2023, 88, 17521.
[23]	(a) Yamane, Y.; Yoshinaga, K.; Sumimoto, M.; Nishikata, T. ACS Catal. 2019, 9, 1757. doi: 10.1021/acscatal.8b04872
[24]	Che, F.; Zhong, J.; Yu, L.; Ma, C.; Yu, C.; Wang, M.; Hou, Z.; Zhang, Y. Adv. Synth. Catal. 2020, 362, 5020.
[25]	(a) Zhang, Z.; Jia, C.; Kong, X.; Hussain, M.; Liu, Z.; Liang, W.; Jiang, L.; Jiang, H.; Ma, J. ACS Sustainable Chem. Eng. 2020, 8, 16463. pmid: 31642675
	(b) Manoharan, R.; Logeswaran, R.; Jeganmohan, M. J. Org. Chem. 2019, 84, 14830. doi: 10.1021/acs.joc.9b02527 pmid: 31642675
[26]	Lu, X.-Y.; Shui, F.-Y.; Zhang, X.; Huang, R.; Wang, Z.-Z.; Song, Y.-W.; Jiang, F.; Yang, G.-X.; Sun, Y.-X. Org. Chem. Front. 2023, 10, 5616.
[27]	(a) Jing, Q.; Qiao, F. C.; Sun, J.; Wang, J. Y.; Zhou, M. D. Org. Biomol. Chem. 2023, 21, 7530. doi: 10.1039/d3ob01240a pmid: 37674373
	(b) Yu, W. Q.; Fan, J. H.; Chen, P.; Xiong, B. Q.; Xie, J.; Tang, K. W.; Liu, Y. Org. Biomol. Chem. 2022, 20, 1958. pmid: 37674373
	(c) Zhong, L.-J.; Chen, H.; Shang, X.; Xiong, B.-Q.; Tang, K.-W.; Liu, Y. J. Org. Chem. 2024, 89, 5409. pmid: 37674373
	(d) Zhang, M.-Z.; Li, W.-T.; Li, Y.-Y.; Wang, Q.; Li, C.; Liu, Y.-H.; Yin, J.-X.; Yang, X.; Huang, H.; Chen, T. J. Org. Chem. 2021, 86, 15544. pmid: 37674373
	(e) Huang, C. M.; Li, J.; Wang, S. L.; Ai, J. J.; Liu, X. Y.; Rao, W. D.; Wang, S. Y. J. Org. Chem. 2021, 86, 8437. pmid: 37674373
[28]	Biswas, P.; Mandal, S.; Guin, J. Org. Lett. 2020, 22, 4294.
[29]	Han, X.; Song, W.; Chen, Y.; Zhou, Z.; Zhang, Z.; Liu, K.; Zeng, X. SynOpen 2023, 7, 154.
[30]	Yang, Z.; Cheng, Y.; Long, J.; Feng, X.; Tang, R.; Wei, J. New J. Chem. 2019, 43, 18760.
[31]	Ma, S.; Zhou, P.; Fan, X.; Li, D.; Yang, J. Tetrahedron Lett. 2022, 102, 153933.

N-芳基丙烯酰胺与自由基级联环化合成2-吲哚酮研究进展

Research Progress on the Synthesis of 2-Oxindoles via Radical Cascade Cyclization of N-Arylacrylamide

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 12

参考文献 31

相关文章 15

编辑推荐

相关统计

本文评价

[1]	祝辉, 吴鹏, 钟晨鸣, 李舒铭, 林钢, 刘雪粉, 罗书平. 供体-受体-供体(D-A-D)型芳香酮设计合成与光催化C(sp³)—H偶联反应性能研究[J]. 有机化学, 2025, 45(9): 3441-3449.
[2]	解人杰, 谢复开, 孙然, 王欣, 王钰佳, 李蕾, 王贺. 电子供体-受体复合物(EDA)介导N-芳基丙烯酰胺与芳基硫鎓盐的自由基环化反应[J]. 有机化学, 2025, 45(8): 2913-2922.
[3]	史茜, 李忠玉, 李晗. 杂环金属铱配合物光敏剂的研究进展[J]. 有机化学, 2025, 45(7): 2389-2405.
[4]	谭永波, 舒洪波, 黄华文. 光诱导N-芳基丙烯酰胺参与的吲哚酮合成研究进展[J]. 有机化学, 2025, 45(6): 2086-2108.
[5]	高根伟, 李震, 李炎, 陆熹. 光/镍协同催化C(sp²)—C(sp³)键构建研究进展[J]. 有机化学, 2025, 45(6): 1905-1919.
[6]	谭燕, 应佳乐, 於兵, 陆展. 可见光促进烯基硅化合物有氧氧化-叠氮化反应[J]. 有机化学, 2025, 45(5): 1684-1690.
[7]	周思成, 刘运奎. P/N-杂配铜(I)光催化剂介导的可见光催化反应进展[J]. 有机化学, 2025, 45(5): 1644-1668.
[8]	陈雨佳, 刘志林, 陈凯, 向皞月, 阳华. 无金属、光催化氧化苄基C—H键以获得羰基官能团[J]. 有机化学, 2025, 45(5): 1755-1762.
[9]	吴利华, 杨建静, 闫克鲁, 许丽荣, 文江伟. 单原子光催化有机合成研究进展[J]. 有机化学, 2025, 45(5): 1591-1613.
[10]	蒋晨阳, 尹艳丽, 江智勇. 光酶催化不对称自由基加成反应研究进展[J]. 有机化学, 2025, 45(5): 1614-1633.
[11]	李顺曦, 游力栩, 李玉龙, 舒伟. 光介导氨及其等价体参与的碳氮成键反应研究进展[J]. 有机化学, 2025, 45(5): 1460-1477.
[12]	黄嘉浩, 黄雅豪, 胡鹏. 氢原子转移介导的光催化C(sp³)—H键氧化反应进展[J]. 有机化学, 2025, 45(5): 1509-1522.
[13]	谭芳芳, 史孟欣, 张文敏, 李洋. 光催化生物质相关转化[J]. 有机化学, 2025, 45(5): 1523-1547.
[14]	林风, 张艳, 吴明, 刘会艳, 郝文娟, 姜波. 利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物[J]. 有机化学, 2025, 45(5): 1729-1738.
[15]	洪洋, 邓红平. 可见光催化的酸性C(sp³)—H键官能团化反应研究进展[J]. 有机化学, 2025, 45(5): 1569-1590.