噁唑酮不同活性位点的官能团化反应研究进展

doi:10.6023/cjoc202506007

有机化学 ›› 2026, Vol. 46 ›› Issue (1): 1-20.DOI: 10.6023/cjoc202506007 上一篇下一篇

综述与进展

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
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

Zhijie Jiang^a, Jinxiu Chen^b^,^c, Xiaofei Zhu^d, Xinhao Deng^c, Qiongjiao Yan^c^,^*(), Wei Wang^b^,^*(), Hui Zhou^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: * E-mail: 875531154@qq.com; wang520520wei@163.com; huizhou@ccnu.edu.cn
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))

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摘要/Abstract

噁唑酮是合成α,α-二取代氨基酸、N,O-缩醛类化合物以及杂环化合物的重要前体, 在有机合成中的应用越来越广泛. 近年来基于噁唑酮的官能团转化合成了一系列重要有机化合物, 特别是利用其不对称转化得到了重要手性化合物. 因此, 涉及噁唑酮转化的反应引起了越来越多科研工作者关注. 基于噁唑酮多活性位点的特性, 按其不同活性位点分类综述了噁唑酮参与的各种有机反应, 包括C-2位、C-4位和C-5位官能团化以及多反应位点的环加成反应. 同时也重点介绍了本课题组最近开发的基于邻苯二甲酰羟胺活性酯原位形成噁唑酮合成手性非天然氨基酸的方法, 与已有的噁唑酮官能团化反应形成优势互补, 促进该领域的蓬勃发展. 最后对该领域所面临的挑战和机遇进行了展望和探讨.

关键词: 噁唑酮, 活性位点, 官能团化, 氨基酸, 不对称转化

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

引用此文

姜志洁, 陈锦秀, 朱晓菲, 邓鑫浩, 严琼姣, 汪伟, 周慧. 噁唑酮不同活性位点的官能团化反应研究进展[J]. 有机化学, 2026, 46(1): 1-20.

Zhijie Jiang, Jinxiu Chen, Xiaofei Zhu, Xinhao Deng, Qiongjiao Yan, Wei Wang, Hui Zhou. 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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图/表 67

图1. 噁唑酮的反应位点

Figure 1. Reaction sites of azlactones

图式1. 噁唑酮与α,β-不饱和酯的C-2选择性加成反应

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

图式2. 噁唑酮与酰基膦酸酯的C-2选择性加成反应

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

图式3. 噁唑酮与邻羟基查尔酮衍生物的区域选择性Michael加成

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

图式4. 噁唑酮与2,3-丁二烯酸酯的加成反应

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

图式5. 铑催化的噁唑酮与炔烃的多米诺噁唑酮炔基化/aza-Cope重排反应

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

图式6. 铱催化的噁唑酮的对映选择性α-烷基化反应

Scheme 6. Iridium catalyzed α-alkylation of azlactones

图式7. 乙烯基异恶唑与噁唑酮的不对称Michael加成反应

Scheme 7. Asymmetric Michael addition reaction of vinylisoxazole and azlactones

图式8. 2H-氮丙啶与噁唑酮的对映选择性反应

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

图式9. 噁唑酮与苯偶氮羧酸酯的不对称胺化反应

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

图式10. 噁唑酮C-4位不对称烯丙基化反应

Scheme 10. C-4 asymmetric allylation of azlactones

图式11. 噁唑酮与不对称非环烯丙基酯的不对称烯丙基化反应

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

图式12. 噁唑酮的对映选择性烯丙基化反应

Scheme 12. Enantioselective allylation reaction of azlactones

图式13. 钯催化的噁唑酮与联烯的加成反应

Scheme 13. Palladium catalyzed addition reaction of azlactones to allenes

图式14. 钯催化噁唑酮与2,3-不饱和吡喃苷反应

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

图式15. 铱催化的噁唑酮C-4位烯丙基化反应

Scheme 15. Iridium catalyzed C-4 allylation of azlactones

图式16. 钯催化噁唑酮与1,3-二烯的烯丙基烷基化反应

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

图式17. 钯催化噁唑酮与1,4-二烯不对称烯丙基烷基化反应

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

图式18. 铱催化噁唑酮的不对称双烯丙基烷基化反应

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

图式19. 钯催化噁唑酮与MBH碳酸酯的不对称烯丙基烷基化反应

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

图式20. 钯催化噁唑酮与异戊二烯的偶联反应

Scheme 20. Pd-catalyzed coupling of azlactones with isoprene

图式21. 钯催化噁唑酮C-4位苄基化反应

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

图式22. 可见光促进噁唑酮自由基偶联反应

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

图式23. 噁唑酮与烷烃C(sp3)—H/C(sp3)—H自由基偶联反应

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

图式24. 炔基碘盐介导噁唑酮炔基化反应

Scheme 24. Alkynyliodonium-mediated alkynylation of azlactones

图式25. 噁唑酮不对称炔基化反应

Scheme 25. Asymmetric alkynylation of azlactones

图式26. 噁唑酮与芳基溴代物C-4位芳基化反应

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

图式27. 噁唑酮与碘试剂的C-4位芳基化反应

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

图式28. 4-吡咯烷基吡啶催化的Steglich重排

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

图式29. 异硫脲催化的对映选择性酰基转移反应

Scheme 29. Isothiourea-catalyzed enantioselective carboxy group transfer reaction

图式30. 双催化策略催化不对称Steglich重排反应

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

图式31. 手性DMAP氮氧化物催化噁唑酮的酰基迁移反应

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

图式32. 噁唑酮与二乙烯基N-酰基吡咯酮的反应

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

图式33. 布朗斯特碱催化噁唑酮与烯酮的Michael加成反应

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

图式34. 噁唑酮与α,β-不饱和三氯甲烷酮的不对称加成反应

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

图式35. 噁唑酮与烯基二烯基酮的不对称加成反应

Scheme 35. Asymmetric addition reaction of azlactones and vinyldienones

图式36. 噁唑酮与烯基二烯基酮的不对称加成反应

Scheme 36. Asymmetric addition reaction of azlactones and vinyldienones

图式37. 噁唑酮与脱氢丙氨酸的不对称加成反应

Scheme 37. Asymmetric addition reaction of azlactones and dehydroalanines

图式38. 噁唑酮与乙烯磺酰氟的对映选择性共轭加成反应

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

图式39. 四氨基膦羧酸盐催化噁唑酮和N-磺酰亚胺的Mannich反应

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

图式40. 噁唑酮与脂肪族亚胺的不对称加成反应

Scheme 40. Asymmetric addition reaction of azlactones with aliphatic imines

图式41. 噁唑酮与N-膦酰亚胺的不对称Mannich反应

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

图式42. 噁唑酮与酮胺的不对称Mannich反应

Scheme 42. Asymmetric Mannich reaction of azlactones and ketoamines

图式43. 噁唑酮和烯醇醚间的分子间烯型反应

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

图式44. 手性膦酸催化烯基吲哚和噁唑酮加成反应

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

图式45. 噁唑酮与不饱和脂肪族醛的不对称催化Aldol反应

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

图式46. 噁唑酮与N-芳基-N-芳基酰肼的不对称胺化反应

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

图式47. 噁唑酮的不对称三氟甲硫基化反应

Scheme 47. Asymmetric trifluoromethylthiolation of azlactones

图式48. 手性DMAP衍生物催化噁唑酮的醇解反应

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

图式49. 脲基双功能催化剂催化噁唑酮的DKR反应

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

图式50. 噁唑酮的硫醇解DKR反应

Scheme 50. Thiolysis-based DKR reaction of azlactones

图式51. 四肽催化甲醇对噁唑酮的DKR反应

Scheme 51. Tetrapeptide catalyzed DKR reaction of methanol with azlactones

图式52. 胺类亲核试剂对噁唑酮的不对称动力学拆分

Scheme 52. Amine nucleophiles for dynamic kinetic resolution of azlactones

图式53. 噁唑酮与缺电子烯烃的对映选择性1,3-偶极环加成反应

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

图式54. 噁唑酮与查尔酮的Hetero-Diels-Alder反应

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

图式55. 噁唑酮与氧杂氮杂环丙烷的氧胺化反应

Scheme 55. Oximation reaction of oxazolone with oxaziridine

图式56. 噁唑酮与亚甲基吲哚啉酮之间的立体选择性1,3-偶极环加成反应

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

图式57. 手性磷酸催化的噁唑酮与亚甲基吲哚啉酮的1,3-偶极环加成反应

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

图式58. 噁唑酮与邻羟基苯乙烯对映选择性[4＋2]环加成反应

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

图式59. 噁唑酮与偶氮萘的不对称[2＋3]环加成反应

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

图式60. 噁唑酮与N-取代β-咔啉的对映选择性环加成反应

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

图式61. 铜催化乙炔基苯并噁唑烷酮和噁唑酮的不对称脱羧[4＋2]环加成

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

图式62. 异靛红与噁唑酮的不对称[3＋2]环加成反应

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

图式63. 噁唑酮与2-苯并噻唑胺的[4＋2]环加成反应

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

图式64. 氮杂邻亚甲基苯醌与噁唑酮的[4＋2]环加成反应

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

图式65. 2-乙烯基苯并噻吩与噁唑酮的[4＋2]环加成反应

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

图式66. 过渡金属催化NHP酯的不对称炔丙基化和烯丙基化反应

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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