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

doi:10.6023/cjoc202501016

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3691-3700.DOI: 10.6023/cjoc202501016 Previous Articles Next Articles

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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)

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

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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.

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Fig. & Tab. 12

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

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

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

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

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

Scheme 5. Synthesis of 2-oxindoles catalyzed by NHN

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

Scheme 7. Synthesis of 2-oxindoles without photocatalyst

Scheme 8. Synthesis of 2-oxindoles using CTC strategy

Scheme 9. Electrocatalytic synthesis of 2-oxindoles

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

Scheme 11. Oxidant-assisted synthesis of 2-oxindol

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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

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