Recent Advances in Cyclization Reactions Using N-Vinylamides

doi:10.6023/cjoc202604012

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (10): 3865-3888.DOI: 10.6023/cjoc202604012 Previous Articles Next Articles

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N-乙烯基酰胺参与的环化反应研究进展

邵长卿^†, 林凯贤^†, 熊毅^†, 何晓雨^*(), 邹有全^*()

武汉大学药学院组合生物合成与新药发现教育部重点实验室组合生物合成与新药发现教育部重点实验室武汉 430071

收稿日期:2026-04-20 修回日期:2026-05-13 发布日期:2026-07-06
通讯作者: 何晓雨, 邹有全
作者简介:
^†共同第一作者.
基金资助:
中央高校基本科研业务费(2042025kf0067); 武汉大学人才启动基金(691000002); 武汉光化学技术研究院基金(GHY2024PY002)

Recent Advances in Cyclization Reactions Using N-Vinylamides

Changqing Shao^†, Kaixian Lin^†, Yi Xiong^†, Xiaoyu He^*(), Youquan Zou^*()

Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071

Received:2026-04-20 Revised:2026-05-13 Published:2026-07-06
Contact: Xiaoyu He, Youquan Zou
About author:
^†These authors contributed equally to this work.
Supported by:
Fundamental Research Funds for the Central Universities(2042025kf0067); Start-up Funding from Wuhan University(691000002); Wuhan Institute of Photochemistry and Technology Grant(GHY2024PY002)

N-Vinylamides are an important class of synthetic building blocks, which are widely used in organic synthesis. Their unique structure, strong reactivity, and diverse reaction pathways make them ideal substrates for constructing cyclic frameworks. This review summarizes the recent progresses on cyclization reactions involving N-vinylamides to construct aminocyclopropanes, oxazolines, oxazoles, pyridines, and other cyclic compounds. The reaction mechanisms, substrate scope, stereoselectivity control, and the application of the products are also discussed.

Key words: enamide, cyclization reaction, aminocyclopropane, heterocyclic compounds, stereoselectivity

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Changqing Shao, Kaixian Lin, Yi Xiong, Xiaoyu He, Youquan Zou. Recent Advances in Cyclization Reactions Using N-Vinylamides[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 3865-3888.

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Fig. & Tab. 51

Scheme 1. (a) Enamides: resonance formula and its reaction site; (b) Representative drugs containing aminocyclopropane or N-contain-ing heterocycles; (c) Cyclization reactions of N-vinylamides

Scheme 2. Stereoselective Simmons-Smith cyclopropanation of chiral enamides

Scheme 3. Ru(II) catalyzed π-facial selective cyclopropanation of chiral enamides

Scheme 4. Ru(II)-catalyzed asymmetric cyclopropanation of enamides

Scheme 5. Ru(II)-catalyzed asymmetric cyclopropanation of N-vinylpyrimidines

Scheme 6. Rh(II)-catalyzed asymmetric cyclopropanation of N-vinylpyrimidines

Scheme 7. Pd-catalyzed oxidative cyclopropanation of enamides

Scheme 8. The Au-catalyzed enantioselective cyclopropanation of enamides

Scheme 9. Rh(I)-catalyzed asymmetric cyclopropanation of enamides

Scheme 10. Photocatalytic intramolecular cyclization of enamides

Scheme 11. [3＋2] cycloaddition of N-vinylamide and 1,1-dibromoformylamine

Scheme 12. [4＋1] cycloaddition of N-vinylamides and sulfur ylides

Scheme 13. Ag-catalyzed [4＋1] cycloaddition of N-vinylamides and sulfur ylides

Scheme 14. IPCT-induced visible-light-catalyzed cyclization of N-vinylamides

Scheme 15. Electrocatalytic cyclization of enamides

Scheme 16. Cyclization reactions of enamides for the construction of oxazole-containing natural products

Scheme 17. PIDA-mediated intramolecular cyclization of enamides

Scheme 18. Hypervalent I-mediated cyclization of enamides

Scheme 19. Ag2CO3-mediated cyclization of enamides

Scheme 20. TFA-mediated cyclization of enamides

Scheme 21. NBS/Me2S-participated thermal cyclization of enamides

Scheme 22. Defluorinative cyclization of enamides with fluoroalkyl halides

Scheme 23. Dase-promoted thermal cyclodebromination of β,β-dibrominated enamides

Scheme 24. Cu-catalyzed intramolecular cyclization of enamides

Scheme 25. Pd-catalyzed cyclization of enamides

Scheme 26. Photocatalytic intramolecular cyclization of enamides

Scheme 27. The Re-catalyzed cycloaddition of enamides with alkynes

Scheme 28. The Ru-catalyzed cycloaddition of enamides with alkynes

Scheme 29. The Cu(II)-catalyzed cyclization of enamides with sulfonylhydrazide

Scheme 30. Cu(I)-catalyzed cycloaddition of enamides with alkynes

Scheme 31. Cr-catalyzed intramolecular cyclization of enamides

Scheme 32. Rh-catalyzed cycloaddition of enamides with alkynes

Scheme 33. Ru-catalyzed cycloaddition of enamides with alkynes

Scheme 34. Cu-catalyzed cyclization of enamides

Scheme 35. Electrocatalytic cyclization of enamides

Scheme 36. Ti-catalyzed cyclization of enamides

Scheme 37. Pd-catalyzed carbonylation of enamides

Scheme 38. Pd with photoredox-catalyzed carbonylation of ena-mides

Scheme 39. Ttransition-metal-free carbonylation of enamides

Scheme 40. CO2-involved carbonylation of enamides

Scheme 41. The Cu-catalyzed carbonylation of enamides with difluorocarbene precursors

Scheme 42. Au-catalyzed intramolecular cycloaddition of enamides

Scheme 43. Cu-catalyzed cyclization of enamides with sulfonyl chlorides

Scheme 44. Metal-free three-component cyclization of enamides

Scheme 45. Cu-catalyzed three-component cyclization of enamides

Scheme 46. Rh(III)-catalyzed [4＋2] cycloaddition of enamides

Scheme 47. BF3•Et2O-catalyzed domino reaction of enamides with aldehydes

Scheme 48. Ru-catalyzed cycloaddition of enamides and aromatic hydroxamic acid esters

Scheme 49. Base-promoted condensative cycloaddition of enamides with o-phenylenediamine

Scheme 50. CPA-catalyzed asymmetric cycloaddition of enamides

Scheme 51. Fe(III)-catalyzed cyclization of enamides with diselenides

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N-乙烯基酰胺参与的环化反应研究进展

Recent Advances in Cyclization Reactions Using N-Vinylamides

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[3]	Pin-Ke Yu, Hai-Yang Liu, Fan Xiao, Xiu-Qin Dong. Recent Progress on Iron-Group Metal-Catalyzed Asymmetric Hydrogenation of Alkenes [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2622-2643.
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[10]	Huanle Li, Qi Pan, Shaojie Lou, Yangjie Mao, Danqian Xu. Recent Advances in Selective C—H Bond Functionalization of Amines Through Hydrogen Atom Transfer (HAT) Process [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3213-3243.
[11]	Ting Mao, Linyuan Zeng, Jilin Wen, Jia Jia. Visible Light-Mediated Iridium-Catalyzed Debromocyclization of Aliphatic α-Bromotrifluoromethyl Groups [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2520-2528.
[12]	Xinyao Sheng, Xinxin Li, Xiao Xing, Ling Pan, Qun Liu, Yifei Li. Synthesis of α-Carbolinone Compounds Based on Tandem Cyclization Reaction of 2-Nitrochalcone and Ethyl Isocyanoacetate [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2163-2170.
[13]	Xun Tian, Guogang Deng, Xiaodong Yang. Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 655-667.
[14]	Jiahong Chen, Jingjing Xu, Hanjing Deng, You Zi. Green Synthesis of Sulfinamides: Mild Oxidative Transformation Using Selectfluor in Water [J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4398-4404.
[15]	Xu Zhang, Peisen Zou, Xiaoqing Liu, Hongyan Bi, Dongliang Mo. Recent Progress in Gold-Catalyzed Intramolecular Cyclization of Alkynes and Its Applications [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3755-3776.