Recent Advances on the Synthesis of Ten-Membered Nitrogen Heterocyclic Compounds

doi:10.6023/cjoc202508004

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 420-442.DOI: 10.6023/cjoc202508004 Previous Articles Next Articles

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十元氮杂环化合物合成最新研究进展

罗艳^a^,^†, 刘章伟^a^,^†, 胡朝蕾^b, 闭红艳^a^,^*(), 莫冬亮^a^,^*()

^a 广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室广西桂林 541004
^b 中国矿业大学力学与土木工程学院(北京) 北京 100083

收稿日期:2025-09-28 修回日期:2025-10-08 发布日期:2025-10-23
通讯作者: 闭红艳, 莫冬亮
作者简介:
^† 共同第一作者
基金资助:
广西自然科学基金(2025GXNSFGA069003); 广西自然科学基金(2023GXNSFDA026025); 国家自然科学基金(22571050); 广西八桂青年学者计划资助项目

Recent Advances on the Synthesis of Ten-Membered Nitrogen Heterocyclic Compounds

Yan Luo^a, Zhangwei Liu^a, Zhaolei Hu^b, Hongyan Bi^a^,^*(), Dongliang Mo^a^,^*()

^a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004
^b School of Mechanics and Civil Engineering, China University of Mining and Technology (Beijing), Beijing 100083

Received:2025-09-28 Revised:2025-10-08 Published:2025-10-23
Contact: Hongyan Bi, Dongliang Mo
About author:
^† These authors contributed equally to this work.
Supported by:
Natural Science Foundation of Guangxi(2025GXNSFGA069003); Natural Science Foundation of Guangxi(2023GXNSFDA026025); National Natural Science Foundation of China(22571050); Guangxi Bagui Youth Program

Ten-membered nitrogen heterocyclic compounds are not only the cores of many nitrogen-containing alkaloids, but also the key intermediates for the construction of other natural products. Consequently, their efficient synthesis has garnered significant attention in the field of organic and medicinal chemistry. Over the past decade, since their special medium-sized rings and possessing good biological activities, the synthetic methodologies toward the preparation of ten-membered N-hetero- cyclic compounds have been greatly developed and have also become one of the hottest topics in the medium-sized ring synthetic fields. This review summarizes the recent advances in the synthesis of ten-membered N-heterocyclic compounds in the last decade. It coveres the innovative synthetic methodologies for these ten-membered nitrogen heterocyclic compounds and their applications in the total synthesis of natural products.

Key words: ten-membered N-heterocyclic compounds, medium-sized ring compounds, cyclization reaction, cycloaddition reaction, ring expansion reaction

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Yan Luo, Zhangwei Liu, Zhaolei Hu, Hongyan Bi, Dongliang Mo. Recent Advances on the Synthesis of Ten-Membered Nitrogen Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 420-442.

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Fig. & Tab. 44

Figure 1. Bioactive compounds and natural products containing ten-membered N-heterocycles

Scheme 1. Oxy-2-aza-Cope ring expansion to form macrocyclic lactams

Scheme 2. Successive ring-expansion (SuRE) methods to prepare ten-membered lactams

Scheme 3. Synthesis of ten-membered lactams via conjugate addition/ring expansion cascade reactions

Scheme 4. Assembly of two 1,3-dipoles for preparing ten-membered N-heterocyclic compounds

Scheme 5. Palladium-catalyzed synthesis of stereodefined ten-membered N-heterocycles from 1,5-bisallenes

Scheme 6. Possible reaction mechanism for carbopalladation of bisallenes

Scheme 7. Cascade reaction of arynes, tertiary amines and aldehydes

Scheme 8. Radical aryl migration enables synthesis of structurally diverse ten-membered N-heterocyclic compounds

Scheme 9. Cascade reaction of thiolactams to prepare ten-membered N-heterocyclic compounds

Scheme 10. Pd-catalyzed asymmetric [6＋4] cycloaddition to synthesize ten-membered N-heterocyclic compounds

Scheme 11. Palladium-catalyzed [6＋4] cycloaddition for the synthesis of ten-membered N-heterocyclic compounds

Scheme 12. Synthesis of ten-membered N-heterocycles via Pd-catalyzed asymmetric higher-order dipolar cycloaddition

Scheme 13. Palladium-catalyzed asymmetric [8＋2] dipolar cycloadditions of vinyl carbamates and ketenes

Scheme 14. Preparing ten-membered N-heterocycles via cycloaddition of α-chloro ene-formamides and cyclic anhydrides

Scheme 15. Synthesis of allene-containing ten-membered N-heterocyclic derivatives

Scheme 16. Synthesis of polyarene-fused ten-membered lactams through high-order [7＋3] cycloaddition reaction

Scheme 17. Ring expansions for the construction of medium sized lactones and lactams

Scheme 18. Synthesis of medium-sized lactams via a tandem oxidative dearomatization-ring expansion reaction

Scheme 19. Synthesis of medium-sized nitrogen heterocycles through migratory ring expansion of metalated ureas

Scheme 20. Synthesis of ten-membered lactams by photocatalytic C—C bond cleavage

Scheme 21. Plausible reaction mechanism

Scheme 22. Electrochemical synthesis of ten-membered lactams

Scheme 23. Synthesis of arene-fused ten-membered lactams via hydrolysis of imidazoline and ring expansion

Scheme 24. Ring expansion of hydrated imidazoline to prepare diarene-fused 1,4,7-ten-memberd ring compounds

Scheme 25. Preparation of ten-membered N-heterocycles through side-chain insertion into thiazepinone scaffolds

Scheme 26. Synthesis of cyclic tripeptides through the ring expansion of 2,5-diketopiperazines

Scheme 27. Synthesis of dibenzodiazepine derived ten-membered ring compounds by Smiles ring expansion

Scheme 28. Cascade cyclization and ring expansion to synthesize ten-membered N-heterocyclic compounds

Scheme 29. Synthesis of medium-sized rings and macrocycles via cyclization/ring expansion cascade reaction

Scheme 30. Synthesis of ten-membered N-heterocyclic-bridged biarenes via a VQM-enabled diversity-oriented strategy

Scheme 31. Gold-catalyzed cyclization reaction of furan-deri- ved alkynes to synthesize ten-membered N-heterocycles

Scheme 32. Plausible mechanism of gold-catalyzed cyclization reaction of furan-derived alkynes

Scheme 33. Yttrium-catalyzed intramolecular cyclization reaction

Scheme 34. Synthesis of ten-membered N-heterocyclic lactones with cyclic diaryliodonium salts

Scheme 35. TfOH-promoted cyclization to prepare ten-membered N-heterocyclic compounds

Scheme 36. Construction of bridged ten-membered N-hetero- cyclic amidines containing trans-double bond through cyclization reaction

Scheme 37. Application of ten-membered ring intermediate in the total synthesis of (－)-protoemetinol

Scheme 38. Application of ring expansion reaction in the total synthesis of (－)-6-Desmethyl-Fluvirucinine A1

Scheme 39. Application of Reformatsky-Aza-Claisen rearrangement in the synthesis of Tabernaemontanine

Scheme 40. Application of ring-distortion strategy in the total synthesis of Yohimbine Y6

Scheme 41. The studies for the synthesis of AST3-88

Scheme 42. Synthesis of ten-membered ring fused polycyclic bisindole alkaloids

Scheme 43. Synthesis of drug LE404

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十元氮杂环化合物合成最新研究进展

Recent Advances on the Synthesis of Ten-Membered Nitrogen Heterocyclic Compounds

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