氮杂环丙烷与不饱和化合物发生[3+2]扩环反应的研究进展

doi:10.6023/cjoc202305008

有机化学 ›› 2023, Vol. 43 ›› Issue (12): 4057-4074.DOI: 10.6023/cjoc202305008 上一篇下一篇

综述与进展

氮杂环丙烷与不饱和化合物发生[3+2]扩环反应的研究进展

郝二军^a^,^*(), 丁笑波^a, 王珂新^a, 周红昊^a, 杨启亮^a, 石磊^a^,^b^,^*()

a 河南师范大学化学化工学院抗病毒性传染病创新药物全国重点实验室平原实验室绿色化学介质与反应教育部重点实验室精细化学品绿色制造河南省协同创新中心河南新乡 453007
b 大连理工大学化学学院精细化工国家重点实验室辽宁大连 116024

收稿日期:2023-05-09 修回日期:2023-07-11 发布日期:2023-08-30
基金资助:
国家自然科学基金(22171036); 国家自然科学基金(22007028); 河南省自然科学基金(232300421126); 河南师范大学化学化工学院开放研究基金(2020YB03)

Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds

Erjun Hao^a,*(), Xiaobo Ding^a, Kexin Wang^a, Honghao Zhou^a, Qiliang Yang^a, Lei Shi^a^,^b,*()

a State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
b State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024

Received:2023-05-09 Revised:2023-07-11 Published:2023-08-30
Contact: *E-mail: hej@htu.edu.cn; shilei17@dlut.edu.cn
Supported by:
National Natural Science Foundation of China(22171036); National Natural Science Foundation of China(22007028); Natural Science Foundation of Henan Province(232300421126); Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University(2020YB03)

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摘要/Abstract

由于具有较强的环张力, 氮杂环丙烷能够与多种不饱和化合物发生[3+2]扩环反应构建氮杂环骨架结构. 这些氮杂环化合物是许多药物、天然产物和生物活性分子的核心结构, 同时也是一类重要的有机反应中间体, 在医药、农业、化工、有机合成等领域具有十分广泛的用途. 近年来, 许多化学研究者以氮杂环丙烷作为合成子, 构建了结构复杂的杂环结构, 促进了氮杂环丙烷领域的快速发展. 对近十年来烯烃、炔烃、醛、酮、腈等含有不饱和键的化合物与氮杂环丙烷发生的[3+2]扩环反应进行了综述, 并对该领域的发展方向进行了展望.

关键词: 氮杂环丙烷, 杂环化合物, [3+2]扩环反应

Due to their high ring strain, aziridines readily undergo ring-expansion reactions, reacting with various unsaturated compounds to form heterocyclic compounds. These heterocyclic compounds serve as important scaffolds for drugs, natural products, and bioactive molecules. Additionally, they are valuable organic intermediates with wide-ranging applications in medicine, agriculture, chemical engineering, organic synthesis, and related fields. In recent years, there has been a significant increase in the synthesis of heterocyclic compounds using aziridines as three-atom synthons, resulting in a rapid advancement of research in this area. This review aims to provide an overview of the most recent [3+2] ring-expansion reactions involving aziridines and unsaturated compounds, such as olefins, aldehydes, ketones, and nitriles, over the past decade. Furthermore, the prospect in this field is also discussed.

Key words: aziridine, heterocyclic compound, [3+2] ring-expansion reaction

引用此文

郝二军, 丁笑波, 王珂新, 周红昊, 杨启亮, 石磊. 氮杂环丙烷与不饱和化合物发生[3+2]扩环反应的研究进展[J]. 有机化学, 2023, 43(12): 4057-4074.

Erjun Hao, Xiaobo Ding, Kexin Wang, Honghao Zhou, Qiliang Yang, Lei Shi. Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4057-4074.

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图/表 59

图式1. 钯催化乙烯基氮杂环丙烷与α,β-不饱和酮的反应

Scheme 1. Pd catalyzed reaction of alkenyl-substituted aziridines with α,β-unsaturated ketones

图式2. Bu2SnI2催化氮杂环丙烷与1,1-二氰基烯烃的[3+2]环加成反应

Scheme 2. Bu2SnI2 catalyzed the [3+2] cycloaddition of aziridine with 1,1-dicyanoolefin

图式3. 钯催化乙烯基氮杂环丙烷与α,β-不饱和酮发生非对称[3+2]环加成反应

Scheme 3. Pd catalyzed asymmetric [3+2] cycloaddition of vinyl aziridine with α,β-unsaturated ketone

图式4. 钯催化氮杂环丙烷与吲哚发生[3+2]环加成反应

Scheme 4. Pd catalyzed [3+2] cycloaddition of aziridine with indole

图式5. 铑催化乙烯基氮杂环丙烷与联烯或联烯胺的[3+2]环加成反应

Scheme 5. Rh catalyzed [3+2] cycloaddition of vinyl aziridine with diene or dienamine

图式6. 铑催化乙烯基氮杂环丙烷与炔的分子间[3+2]环加成反应

Scheme 6. Rh catalyzed intermolecular [3+2] cycloaddition of vinyl aziridine with alkynes

图式7. 金(I)/路易斯酸接力催化氮杂环丙烷和炔醇及酰胺的[3+2]环加成反应

Scheme 7. Au(I)/Lewis acid relay catalyzed relay [3+2] cycloaddition of aziridine with alkynol and amide

图式8. 钛催化的N-酰氮杂环丙烷与烯烃的[3+2]环加成反应

Scheme 8. Ti catalyzed [3+2] cycloaddition reaction of N-acyl aziridine with olefins

图式9. N-酰基氮杂环丙烷和烯烃的[3+2]环加成机理

Scheme 9. Mechanism of [3+2] cycloaddition of N-acylaziri- dines and alkenes

图式10. 钯催化的乙烯基氮杂环丙烷与缺电子吲哚的去芳构化[3+2]环加成反应

Scheme 10. Pd catalyzed dearomatization [3+2] cycloaddition of vinyl aziridine with electron-deficient indole

图式11. 铑催化的烯基氮杂环丙烷与炔胺的[3+2]环加成反应

Scheme 11. Rh catalyzed [3+2] cycloaddition of alkenyl aziridine with alkynylamine

图式12. 铑催化乙烯基氮杂环丙烷与硅烯醇醚的[3+2]环加成反应

Scheme 12. Rh catalyzed [3+2] cycloaddition of vinyl aziridine with silanol ether

图式13. 钯催化3-硝基吲哚与乙烯基氮杂环丙烷的[3+2]环加成反应

Scheme 13. Pd catalyzed [3+2] cycloaddition of 3-nitroindole with vinyl aziridine

图式14. 钯催化3-硝基吲哚与乙烯基氮杂环丙烷的不对称 [3+2]环加成

Scheme 14. Pd catalyzed asymmetric [3+2] cycloaddition of 3-nitroindole with vinyl aziridine

图式15. 铑催化乙烯基氮杂环丙烷和炔烃的[3+2]环加成反应

Scheme 15. Rh catalyzed [3+2] cycloaddition of vinyl aziridine with alkyne

图式16. 钯催化乙烯基氮杂环丙烷与磺酰基吲哚的[3+2]环加成反应

Scheme 16. Pd catalyzed [3+2] cycloaddition reaction of vinyl aziridine with sulfonyl indole

图式17. 铜催化外消旋氮丙啶与汉斯酯的不对称[3+2]环化反应

. Schemem 17 Asymmetric [3+2] cyclization of racemic aziridine with Hantzsch Esters catalyzed by Cu

图式18. 金和镝接力催化氮杂环丙烷和炔烃的不对称[3+2]环化反应

Scheme 18. Au/Dy relay catalyzed relay asymmetric [3+2] cyclization of aziridine and alkyne

图式19. 金催化氮杂环丙烷和氰化物的[3+2]环化反应

Scheme 19. Au catalyzed [3+2] cyclization of aziridine and cyanide

图式20. 乙烯基氮杂环丙烷分子内[3+2]环加成

Scheme 20. Intramolecular [3+2] cycloaddition of vinyl aziridine

图式21. MgI2催化氮杂环丙烷与烯烃的[3+2]环加成反应

Scheme 21. MgI2 catalyzed [3+2] cycloaddition of aziridines with alkenes

图式22. 镁催化内消旋氮杂环丙烷与C3-烷基吲哚发生[3+2]环加成反应

Scheme 22. Mg catalyzed [3+2] cycloaddition of racemic aziridine with C3-alkylindole

图式23. (C6F5S)2催化乙烯基氮杂环丙烷与多种烯烃的[3+2]环化反应

Scheme 23. (C6F5S)2 catalyzed [3+2] cyclization of vinyl aziridine with various olefins

图式24. 1-(1-苄基-1H-四唑-5-基)丙二烯与氮杂环丙烷的[3+2]环化反应

Scheme 24. [3+2] cyclization of 1-(1-benzyl-1H-tetrazole-5-yl) propadiene with aziridine

图式25. 吲哚与乙烯基氮杂环丙烷的[3+2]环加成反应

Scheme 25. [3+2] cycloaddition of indoles with vinyl aziridines

图式26. 镝催化氮杂环丙烷与多种吡喃和其他开环烯醇醚的不对称[3+2]环加成反应

Scheme 26. Dy catalyzed asymmetric [3+2] cycloaddition of aziridine with pyrans and other ring-opening enol ethers

图式27. 亚胺与氮杂环丙烷的[3+2]环化反应

Scheme 27. [3+2] cyclization of imine with aziridine

图式28. 铟催化二烷基2-(2-(1-甲苯基)苯亚甲基)丙二酸酯的[3+2]环化反应

Scheme 28. In catalyzed [3+2] cyclization of dialkyl 2-(2-(1- tolyl)phenylmethylene)

图式29. 氮杂环丙烷与芳基炔和芳基重氮化合物的无金属级联反应

Scheme 29. Metal-free cascade reaction of aziridines with arylalkynes and aryldiazoniums

图式30. 可见光催化的乙烯基环丙烷和对甲苯基苯并氮杂环丙烷与烯烃的[3+2]环化反应

Scheme 30. Visible photocatalytic [3+2] cyclization of vinyl cyclopropane and p-tolyl benzaziridine with olefins

图式31. N-甲基氮杂环丙烷与烯烃的[3+2]环加成反应

Scheme 31. [3+2] cycloaddition of N-methyl aziridine with olefins

图式32. 由亚胺直接合成γ-内酰胺

Scheme 32. Direct synthesis of γ-lactam from imine

图式33. 路易斯酸催化氮丙啶与带有吸电子基团的吲哚的[3+2]环化反应

Scheme 33. Lewis acid catalyzed [3+2] cyclization of aziridine with indole with electron-withdrawing group

图式34. 碘化锂的催化氮丙啶与缺电子烯烃的[3+2]环加成反应

Scheme 34. LiI catalyzed [3+2] cycloaddition of aziridine with electron-deficient olefins

图式35. 钇催化氮杂环丙烷与亚胺发生[3+2]环加成反应

Scheme 35. Y catalyzed [3+2] cycloaddition of aziridine with imine

图式36. 钛催化2-三氟甲基-N-对甲苯磺酰基氮杂环丙烷与腈的[3+2]环加成反应

Scheme 36. Ti catalyzed [3+2] cycloaddition of 2-trifluoro- methyl-N-p-toluenesulfonyl aziridine with nitrile

图式37. 钯催化乙烯基氮杂环丙烷与环状N-磺酰亚胺发生了[3+2]环加成反应

Scheme 37. Pd catalyzed [3+2] cycloaddition reaction of vinyl aziridine with cyclic N-sulfonimide

图式38. 铑催化氮杂环丙烷与酮胺衍生物发生[3+2]环加成反应

Scheme 38. Rh catalyzed [3+2] cycloaddition of aziridine with ketoamine derivatives

图式39. DBU催化螺氮杂环与丙二腈[3+2]-环加成反应

Scheme 39. DBU catalyzed the [3+2]-cycloaddition of spirazaheterocycle with malononitrile

图式40. 多孔磷酸锆盐催化氮杂环丙烷与CO2的[3+2]环加成反应

Scheme 40. Porous zirconium phosphate catalyzed [3+2] cycloaddition of aziridine with CO2

图式41. 铬催化氮杂环丙烷和二氧化碳高选择性偶联生成5取代噁唑烷酮

Scheme 41. Cr catalyzed highly selective coupling of aziridine and carbon dioxide to produce 5-substituted oxazolidinone

图式42. 铬催化氮杂环丙烷和二氧化碳的反应机理

Scheme 42. Reaction mechanism of aziridine and carbon dioxide catalyzed by Cr

图式43. 钯催化噁唑啉的氮杂环丙烷发生分子内环化

Scheme 43. Pd catalyzed intramolecular cyclization of aziridine of oxazoline

图式44. 钴催化二氧化碳与末端氮杂环丙烷的偶联反应

Scheme 44. Co catalyzed coupling reaction of carbon dioxide with terminal aziridine

图式45. 2-(杂)芳基-N-甲苯磺酰胺与α,β-不饱和醛的立体转化

Scheme 45. Stereoconversion of 2-(hetero)aryl-N-toluenesul- fonamide with α,β-unsaturated aldehyde

图式46. 铁卟啉复合物催化氮杂环丙烷和羰基化合物的[3+2]环加成

Scheme 46. Fe porphyrin complex catalyzed [3+2] cycloaddition of aziridine with carbonyl compounds

图式47. TPPH2/TBACl催化体系催化氮杂环丙烷和二氧化碳[3+2]环加成

Scheme 47. TPPH2/TBACl catalytic system catalyzed [3+2] cyclization of aziridine with CO2

图式48. 高铁酸铵催化氮杂环丙烷和二氧化碳偶联

Scheme 48. Ammonium ferrate catalyzed coupling of aziridine and carbon dioxide

图式49. 氮杂环卡宾催化CO2与N-对甲苯磺酰基氮杂环丙烷的反应

Scheme 49. NHC catalyzed the reaction of CO2 with N-p-to- luenesulfonyl aziridine

图式50. NHC-CO2加合物催化CO2与氮杂环丙烷的[3+2]环加成

Scheme 50. NHC-CO2 adduct catalyzed the [3+2] cycloaddition of CO2 with aziridine

图式51. CO2与氮杂环丙烷偶合反应

Scheme 51. Coupling reaction of CO2 with aziridine

图式52. 甘蔗渣和碘化钾催化氮杂环丙烷和CO2反应合成噁唑烷酮

Scheme 52. Synthesis of oxazolidinone from aziridine and CO2 catalyzed by SCB and KI

图式53. N-杂环烯烃催化氮杂环丙烷与二氧化碳的环加成

Scheme 53. N-heterocyclic olefins catalyzed the cycloaddition of aziridine with CO2

图式54. 氮杂环丙烷与CO2的加成

Scheme 54. Addition of aziridine with CO2

图式55. 二氧化碳和氮杂环丙烷偶联合成噁唑烷酮

Scheme 55. Oxazolidinone synthesis by the coupling of carbon dioxide and aziridines

图式56. 铝络合物二氧化碳和氮杂环丙烷偶联反应机理

Scheme 56. Coupling reaction mechanism of aluminum complex carbon dioxide and aziridine

图式57. 路易斯酸催化含有芳基氮杂环丙烷和烷基异硫氰酸酯的DROC反应

Scheme 57. Lewis acid catalyzed the DROC reaction containing aryl aziridine and alkyl isothiocyanate

图式58. 铝催化的未活化的手性氮杂环丙烷与异硫氰酸酯的[3+2]环加成反应

Scheme 58. Al catalyzed [3+2] cycloaddition of unactivated chiral aziridine with isothiocyanate

图式59. 对位取代的苯乙烯直接合成2-亚氨基噻唑烷

Scheme 59. Direct synthesis of 2-iminothiazolidine from p- substituted styrene

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氮杂环丙烷与不饱和化合物发生[3+2]扩环反应的研究进展

Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds

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