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

doi:10.6023/cjoc202305008

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4057-4074.DOI: 10.6023/cjoc202305008 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 59

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 32. Direct synthesis of γ-lactam from imine

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

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

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

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

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

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

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

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

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

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

Scheme 43. Pd catalyzed intramolecular cyclization of aziridine of oxazoline

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

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

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

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

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

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

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

Scheme 51. Coupling reaction of CO2 with aziridine

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

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

Scheme 54. Addition of aziridine with CO2

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

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

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

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

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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