Recent Advances on the Functionalization of Azlactones at Different Reactive Sites

doi:10.6023/cjoc202506007

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (1): 1-20.DOI: 10.6023/cjoc202506007 Previous Articles Next Articles

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噁唑酮不同活性位点的官能团化反应研究进展

姜志洁^a^,^†, 陈锦秀^b^,^c^,^†, 朱晓菲^d, 邓鑫浩^c, 严琼姣^c^,^*(), 汪伟^b^,^*(), 周慧^b^,^*()

^a 陕西学前师范学院生物食品与化学学院西安 710100
^b 华中师范大学化学学院武汉 430079
^c 武汉工程大学药物研究院武汉 430205
^d 平武中学四川绵阳 621000

收稿日期:2025-07-15 修回日期:2025-08-19 发布日期:2025-09-11
通讯作者: 严琼姣, 汪伟, 周慧
作者简介:
^† 共同第一作者
基金资助:
湖北省自然科学基金(2025AFB675); 2024年度陕西高校优秀青年杰出人才支持计划(2025QJ-02(内))

Recent Advances on the Functionalization of Azlactones at Different Reactive Sites

Jiang Zhijie^a, Chen Jinxiu^b^,^c, Zhu Xiaofei^d, Deng Xinhao^c, Yan Qiongjiao^c^,^*(), Wang Wei^b^,^*(), Zhou Hui^b^,^*()

^a College of Biology, Food and Chemistry, Shaanxi Xueqian Normal University, Xi'an 710100
^b College of Chemistry, Central China Normal University, Wuhan 430079
^c Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
^d Pingwu High School, Mianyang, Sichuan 621000

Received:2025-07-15 Revised:2025-08-19 Published:2025-09-11
Contact: Yan Qiongjiao, Wang Wei, Zhou Hui
About author:
^† The authors contributed equally to this work
Supported by:
Natural Science Foundation of Hubei Province(2025AFB675); 2024 Shaanxi Higher Education Institutions Outstanding Young Talents Support Program(2025QJ-02(内))

Azlactones constitute a crucial precursor for the preparation of α,α-disubstituted amino acids, N,O-acetal derivatives, many heterocyclic compounds, finding increasingly widespread applications in organic chemistry. Recent advances in functionalization of azlactone have enabled the synthesis of many important organic compounds. Notably, asymmetric transformations of azlactone have facilitated the preparation of valuable chiral compounds, attracting growing interest among researchers in this field. Focusing on the multi-active-site nature of azlactone, this review classifies its participation in diverse organic reactions, including C-2, C-4, and C-5 functionalization and multi-site cycloaddition reactions. Meanwhile, our research group has recently developed a novel method for the in situ formation of azlactones via the intramolecular cyclization of N-hydroxyphthalimide esters, which yields a various of chiral unnatural amino acids. This strategy complements existing azlactone functionalization reactions, thereby promoting the robust development of this field. Finally, the challenges and opportunities in this field are critically assessed, providing insights to direct future research and innovation.

Key words: azlactones, reactive site, functionalization, amino acids, asymmetric transformation

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Jiang Zhijie, Chen Jinxiu, Zhu Xiaofei, Deng Xinhao, Yan Qiongjiao, Wang Wei, Zhou Hui. Recent Advances on the Functionalization of Azlactones at Different Reactive Sites[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 1-20.

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Fig. & Tab. 67

Figure 1. Reaction sites of azlactones

Scheme 1. C-2 selective addition of azlactones to α,β-unsa- turated ester surrogates

Scheme 2. C-2 selective addition of azlactones to acyl phosphonates

Scheme 3. Regional selective Michael addition of azlactones and ortho hydroxychalcone derivatives

Scheme 4. Addition reaction of azlactones with 2,3-butanoate compounds

Scheme 5. Rhodium-catalyzed domino alkynylation of oxazolones with alkynes/aza-Cope rearrangements

Scheme 6. Iridium catalyzed α-alkylation of azlactones

Scheme 7. Asymmetric Michael addition reaction of vinylisoxazole and azlactones

Scheme 8. Enantioselective reaction of 2H‑azirines with azlactones

Scheme 9. Asymmetric amination reaction of azlactones and phenylazo carboxylic acid ester

Scheme 10. C-4 asymmetric allylation of azlactones

Scheme 11. Enantioselective allylations of azlactones with unsymmetrical acyclic allyl esters

Scheme 12. Enantioselective allylation reaction of azlactones

Scheme 13. Palladium catalyzed addition reaction of azlactones to allenes

Scheme 14. Palladium-catalyzed reaction between azlactones and 2,3-unsaturated pyranoside

Scheme 15. Iridium catalyzed C-4 allylation of azlactones

Scheme 16. Palladium catalyzed allylic alkylation of azlactones with 1,3-diene

Scheme 17. Asymmetric allyl alkylation of azlactones with 1,4- diene by palladium catalyst

Scheme 18. Iridium-catalyzed asymmetric double allylic alkylation of azlactones

Scheme 19. Palladium-catalyzed asymmetric allylic alkylation of azlactones with MBH carbonates

Scheme 20. Pd-catalyzed coupling of azlactones with isoprene

Scheme 21. Palladium-catalyzed C-4 benzylation of azlactones

Scheme 22. Visible-light-driven radical-coupling reaction of azlactones

Scheme 23. C(sp3)—H/C(sp3)—H CDC reaction of azlactones with alkanes

Scheme 24. Alkynyliodonium-mediated alkynylation of azlactones

Scheme 25. Asymmetric alkynylation of azlactones

Scheme 26. C-4 arylation of azlactones with aryl bromide

Scheme 27. C-4 arylation of azlactones with iodine reagents

Scheme 28. Steglich rearrangement catalyzed by the 4-(pyrro- lidino)pyridine

Scheme 29. Isothiourea-catalyzed enantioselective carboxy group transfer reaction

Scheme 30. Dual-catalysis approach to the asymmetric Steglich rearrangement

Scheme 31. Chiral DMAP-nitroxide catalyzed acyl migration reaction of azlactones

Scheme 32. Reaction between azlactones and dienyl N‑acyl- pyrroles

Scheme 33. Brønsted-base-catalyzed Michael-type addition of azlactones to enones

Scheme 34. Asymmetric addition reaction of azlactones with α,β-unsaturated trichloromethane ketones

Scheme 35. Asymmetric addition reaction of azlactones and vinyldienones

Scheme 36. Asymmetric addition reaction of azlactones and vinyldienones

Scheme 37. Asymmetric addition reaction of azlactones and dehydroalanines

Scheme 38. Enantioselective addition reaction of azlactones with ethylene sulfonyl fluoride

Scheme 39. Mannich-type reaction between azlactones and N- sulfonyl imines catalyzed by a tetraaminophosphonium carboxylate

Scheme 40. Asymmetric addition reaction of azlactones with aliphatic imines

Scheme 41. Asymmetric Mannich-type reaction of N-phos- phonyl imines with azlactones

Scheme 42. Asymmetric Mannich reaction of azlactones and ketoamines

Scheme 43. Intermolecular enol type reaction between oxazolone and enol ethers

Scheme 44. Addition of azlactones to 3-vinylindoles catalyzed by chiral phosphoric acid

Scheme 45. Asymmetric catalytic Aldol reaction between azlactones and unsaturated aliphatic aldehydes

Scheme 46. Asymmetric amination of azlactones with N-aryl- N'-aryl hydrazides

Scheme 47. Asymmetric trifluoromethylthiolation of azlactones

Scheme 48. Chiral DMAP derivative catalyzed the deracemization/ring opening of azlactones

Scheme 49. Dynamic kinetic resolution of azlactones by urea- based bifunctional organocatalysts

Scheme 50. Thiolysis-based DKR reaction of azlactones

Scheme 51. Tetrapeptide catalyzed DKR reaction of methanol with azlactones

Scheme 52. Amine nucleophiles for dynamic kinetic resolution of azlactones

Scheme 53. Enantioselective 1,3-dipolar cycloadditions of azl- actones with electron-deficient alkenes

Scheme 54. Hetero-Diels-Alder reaction between azlactones and chalcones

Scheme 55. Oximation reaction of oxazolone with oxaziridine

Scheme 56. Stereoselective 1,3-dipolar cycloaddition between azlactones and methylene indolinones

Scheme 57. 1,3-Dipolar cycloaddition reaction of azlactones and methylene indolone catalyzed by chiral phosphoric acid

Scheme 58. Enantioselective [4＋2] cycloaddition of azlactones with o-hydroxystyrenes

Scheme 59. Asymmetric [2＋3] cycloaddition reaction between azlactones and azonaphthalenes

Scheme 60. Enantioselective cycloaddition reaction of azlactones with N-substituted β-carboline

Scheme 61. Copper catalyzed enantioselective decarboxylative [4＋2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones

Scheme 62. Catalytic asymmetric formal [3＋2] cycloaddition of isatogens with azlactones

Scheme 63. [4＋2] cycloaddition reaction of azlactones with 2-benzothiazole amines

Scheme 64. [4＋2] cyclization of aza-o-quinone methides with azlactones

Scheme 65. [4＋2] annulation reaction of 2-vinylbenzothiazoles and azlactones

Scheme 66. Transition metal catalyzed asymmetric propargylic and allylic reactions of NHP esters

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噁唑酮不同活性位点的官能团化反应研究进展

Recent Advances on the Functionalization of Azlactones at Different Reactive Sites

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