Citation: Wu Yali, Zhou Xuesong, Xiao Wenjing, Chen Jiarong. Recent Progress in Applications of Vinylaziridines in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3760-3776. doi: 10.6023/cjoc202003061 shu

Recent Progress in Applications of Vinylaziridines in Organic Synthesis

College of Chemistry, Central China Normal University, Wuhan 430079

Corresponding author: Chen Jiarong, chenjiarong@mail.ccnu.edu.cn
Received Date: 27 March 2020
Revised Date: 26 April 2020
Available Online: 30 April 2020
Fund Project: the National Natural Science Foundation of China 91856119Project supported by the National Natural Science Foundation of China (Nos. 21971081, 91856119)the National Natural Science Foundation of China 21971081

Figures(45)

Due to its alkene moiety and highly strained aziridine scaffold, vinylaziridines represent a versatile type of synthetic building blocks and can undergo various chemcial transformations. These transformations enabled facile synthesis of a wide range of nitrogen-containing compounds, especially diverse nitrogen heterocycles, inculding azetidines, pyrrolidines, piperidines, azacycloheptanes and so on. Moreover, development of simple and efficient synthetic methods for various substituted vinylaziridines, stimulating their applications in the fields of organic synthesis, medicinal and agrochemistry, as well as fine chemistry. In recent years, such type of reagents continue to attract considerable research efforts from chemists and enjoyed rapid development. The representative examples of nucleophilic ring-opening and cyclization reactions of vinyl-aziridines over the past five years are summarized. Moreover, the prospects of further development are also disscussed.
- vinylaziridines,
- aziridines,
- ring-opening reaction,
- cyclization reaction,
- nitrogen heterocycles
1. [1]
  Lawrence, S. A. Amines: Synthesis Properties and Applications, Cambridge University Press, Cambridge, 2008, p. 371.
2. [2]
  Das, P.; Delost, M. D.; Qureshi, M. H.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2019, 62, 4265. doi: 10.1021/acs.jmedchem.8b01610
3. [3]
  Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b
4. [4]
  Naito, T. Chem. Pharm. Bull. 2008, 56, 1367. doi: 10.1248/cpb.56.1367
5. [5]
  Bariwal, J.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 9283. doi: 10.1039/c3cs60228a
6. [6]
  Kim, H.; Chang, S. ACS Catal. 2016, 6, 2341. doi: 10.1021/acscatal.6b00293
7. [7]
  Trowbridge, A.; Walton, S. M.; Gaunt, M. J. Chem. Rev. 2020, 120, 2613. doi: 10.1021/acs.chemrev.9b00462
8. [8]
  Yuan, J.-W.; Liu, C.; Lei, A.-W. Chem. Commun. 2015, 51, 1394. doi: 10.1039/C4CC08116A
9. [9]
  Ye, Z.; Zhang, F. Chin. J. Chem. 2019, 37, 513. doi: 10.1002/cjoc.201900049
10. [10]
  Heo, Y. M.; Paek, S. M. Molecules 2013, 18, 9650. doi: 10.3390/molecules18089650
11. [11]
  Ohno, H. Chem. Rev. 2014, 114, 7784. doi: 10.1021/cr400543u
12. [12]
  Ilardi, E. A.; Njardarson, J. T. J. Org. Chem. 2013, 78, 9533. doi: 10.1021/jo401776s
13. [13]
  Feng, J.-J.; Zhang, J. ACS Catal. 2016, 6, 6651. doi: 10.1021/acscatal.6b02072
14. [14]
  Ling, J.; Lam, S. K.; Lo, B.; Lam, S.; Wong, W.-T.; Sun, J.; Chen, G.; Chiu, P. Org. Chem. Front. 2016, 3, 457. doi: 10.1039/C5QO00333D
15. [15]
  Lin, T.-Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Org. Lett. 2017, 19, 2897. doi: 10.1021/acs.orglett.7b01136
16. [16]
  Lin, T.-Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. ACS Catal. 2017, 7, 4047. doi: 10.1021/acscatal.7b00870
17. [17]
  Trost, B. M.; Osipov, M.; Dong, G.-B. J. Am. Chem. Soc. 2010, 132, 15800. doi: 10.1021/ja1071509
18. [18]
  Wang, G.; Franke, J.; Ngo, C. Q.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 7915. doi: 10.1021/jacs.5b04404
19. [19]
  Mei, G.-J.; Yu, L.; Zhu, Z.-Q.; Sun, M.; Shi, F. Synthesis 2018, 51, 1655.
20. [20]
  Yin, J. X.; Mekelburg, T.; Hyland, C. Org. Biomol. Chem. 2014, 12, 9113. doi: 10.1039/C4OB01786B
21. [21]
  Blackham, E. E.; Knowles, J. P.; Burgess, J.; Booker-Milburn, K. I. Chem. Sci. 2016, 7, 2302. doi: 10.1039/C5SC04062K
22. [22]
  Kong, L.; Biletskyi, B.; Nuel, D.; Clavier, H. Org. Chem. Front. 2018, 5, 1600. doi: 10.1039/C8QO00173A
23. [23]
  Sanz, X.; Lee, G. M.; Pubill-Ulldemolins, C.; Bonet, A.; Gulyás, H.; Westcott, S. A.; Bo, C.; Fernández, E. Org. Biomol. Chem. 2013, 11, 7004. doi: 10.1039/c3ob41328d
24. [24]
  Salvado, O.; Gava, R.; Fernandez, E. Org. Lett. 2019, 21, 9247. doi: 10.1021/acs.orglett.9b03672
25. [25]
  Kang, D.; Kim, T.; Lee, H.; Hong, S. Org. Lett. 2018, 20, 7571. doi: 10.1021/acs.orglett.8b03309
26. [26]
  Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857. doi: 10.1016/S0040-4039(00)61948-2
27. [27]
  Spears, G. W.; Nakanishi, K.; Ohfune, Y. Synlett 1991, 91.
28. [28]
  Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5977. doi: 10.1021/jo025747h
29. [29]
  Lowe, M. A.; Ostovar, M.; Ferrini, S.; Chen, C. C.; Lawrence, P. G.; Fontana, F.; Calabrese, A. A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011, 50, 6370. doi: 10.1002/anie.201101389
30. [30]
  Arena, G.; Chen, C. C.; Leonori, D.; Aggarwal, V. K. Org. Lett. 2013, 15, 4250. doi: 10.1021/ol4020333
31. [31]
  Xu, C.-F.; Zheng, B.-H.; Suo, J.-J.; Ding, C.-H.; Hou, X.-L. Angew. Chem., Int. Ed. 2015, 54, 1604. doi: 10.1002/anie.201409467
32. [32]
  Yuan, Z.; Wei, W.; Lin, A.; Yao, H. Org. Lett. 2016, 18, 3370. doi: 10.1021/acs.orglett.6b01512
33. [33]
  Li, T.-R.; Cheng, B.-Y.; Fan, S.-Q.; Wang, Y.-N.; Lu, L.-Q.; Xiao, W.-J. Chem. Eur. J. 2016, 22, 6243. doi: 10.1002/chem.201600735
34. [34]
  Rivinoja, D. J.; G, Y. S.; Gardiner, M. G.; Ryan, J. H.; Hyland, C. J. T. ACS Catal. 2017, 7, 1053. doi: 10.1021/acscatal.6b03248
35. [35]
  Suo, J.-J.; Liu, W.; Du, J.; Ding, C.-H.; Hou, X.-L. Chem. Asian J. 2018, 13, 959. doi: 10.1002/asia.201800133
36. [36]
  Zhang, J.-Q.; Tong, F.; Sun, B.-B.; Fan, W.-T.; Chen, J.-B.; Hu, D.; Wang, X.-W. J. Org. Chem. 2018, 83, 2882. doi: 10.1021/acs.joc.8b00046
37. [37]
  Spielmann, K.; van der Lee, A.; de Figueiredo, R. M.; Campagne, J.-M. Org. Lett. 2018, 20, 1444. doi: 10.1021/acs.orglett.8b00228
38. [38]
  Spielmann, K.; Tosi, E.; Lebrun, A.; Niel, G.; van der Lee, A.; de Figueiredo, R. M.; Campagne, J.-M. Tetrahedron 2018, 74, 6497. doi: 10.1016/j.tet.2018.09.040
39. [39]
  Feng, J.-J.; Lin, T.-Y.; Wu, H.-H.; Zhang, J. J. Am. Chem. Soc. 2015, 137, 3787. doi: 10.1021/jacs.5b01305
40. [40]
  Feng, J.-J.; Lin, T.-Y.; Wu, H.-H.; Zhang, J. L. Angew. Chem., Int. Ed. 2015, 54, 15854. doi: 10.1002/anie.201509185
41. [41]
  Feng, J.-J.; Lin, T.-Y.; Zhu, C.-Z.; Wang, H.; Wu, H.-H.; Zhang, J. L. J. Am. Chem. Soc. 2016, 138, 2178. doi: 10.1021/jacs.6b00386
42. [42]
  Zhang, X.; Zou, H.; Huang, G. ChemCatChem 2016, 8, 2549. doi: 10.1002/cctc.201600349
43. [43]
  Hirner, J. J.; Roth, K. E.; Shi, Y.; Blum, S. A. Organometallics 2012, 31, 6843. doi: 10.1021/om300671j
44. [44]
  Lin, T.-Y.; Zhu, C.-Z.; Zhang, P.; Wang, Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 10844. doi: 10.1002/anie.201605530
45. [45]
  Zhu, C.-Z.; Feng, J.-J.; Zhang, J. Chem. Commun. 2018, 54, 2401. doi: 10.1039/C8CC00279G
46. [46]
  Zhu, C.-Z.; Feng, J.-J.; Zhang, J. L. Angew. Chem., Int. Ed. 2017, 56, 1351. doi: 10.1002/anie.201609608
47. [47]
  Zhu, C.-Z.; Feng, J.-J.; Zhang, J. Chem. Commun. 2017, 53, 4688. doi: 10.1039/C7CC02078C
48. [48]
  Lin, T.-Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Org. Lett. 2018, 20, 3587. doi: 10.1021/acs.orglett.8b01378
49. [49]
  Wan, S.-H.; Liu, S.-T. Tetrahedron 2019, 75, 1166. doi: 10.1016/j.tet.2019.01.022
50. [50]
  Ghorai, M. K.; Tiwari, D. P. J. Org. Chem. 2010, 75, 6173. doi: 10.1021/jo101004x
51. [51]
  Lin, T.-Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Org. Lett. 2017, 19, 6526. doi: 10.1021/acs.orglett.7b03232
52. [52]
  Jiang, F.; Yuan, F.-R.; Jin, L.-W.; Mei, G.-J.; Shi, F. ACS Catal. 2018, 8, 10234. doi: 10.1021/acscatal.8b03410
53. [53]
  Lam, S. K.; Lam, S.; Wong, W.-T.; Chiu, P. Chem. Commun. 2014, 50, 1738. doi: 10.1039/c3cc48266a
54. [54]
  Wani, I. A.; Sayyad, M.; Ghorai, M. K. Chem. Commun. 2017, 53, 4386. doi: 10.1039/C7CC01033H
55. [55]
  Pradhan, S.; Shahi, C. K.; Bhattacharyya, A.; Chauhan, N.; Ghorai, M. K. Org. Lett. 2017, 19, 3438. doi: 10.1021/acs.orglett.7b01397
56. [56]
  Mal, A.; Wani, I. A.; Goswami, G.; Ghorai, M. K. J. Org. Chem. 2018, 83, 7907. doi: 10.1021/acs.joc.8b00788
57. [57]
  Wang, Y.-N.; Li, T.-R.; Zhang, M.-M.; Cheng, B.-Y.; Lu, L.-Q.; Xiao, W.-J. J. Org. Chem. 2016, 81, 10491. doi: 10.1021/acs.joc.6b00991
58. [58]
  Du, Z.-T.; Shao, Z.-H. Chem. Soc. Rev. 2013, 42, 1337. doi: 10.1039/C2CS35258C
59. [59]
  Naesborg, L.; Tur, F.; Meazza, M.; Blom, J.; Halskov, K. S.; Jørgensen, K. A. Chem. Eur. J. 2017, 23, 268. doi: 10.1002/chem.201604995
60. [60]
  Chen, Z.-C.; Chen, Z.; Yang, Z.-H.; Guo, L.; Du, W.; Chen, Y.-C. Angew. Chem., Int. Ed. 2019, 58, 15021. doi: 10.1002/anie.201907797
61. [61]
  Denes, F.; Pichowicz, M.; Povie, G.; Renaud, P. Chem. Rev. 2014, 114, 2587. doi: 10.1021/cr400441m
62. [62]
  Taniguchi, T. Synthesis 2017, 49, 3511. doi: 10.1055/s-0036-1588481
63. [63]
  Miura, K.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5135. doi: 10.1016/S0040-4039(00)80701-7
64. [64]
  Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. doi: 10.1021/ja00218a050
65. [65]
  Hashimoto, T.; Takino, K.; Hato, K.; Maruoka, K. Angew. Chem., Int. Ed. 2016, 55, 8081. doi: 10.1002/anie.201602723
66. [66]
  Hu, X.-Q.; Chen, J.-R.; Wei, Q.; Liu, F.-L.; Deng, Q.-H.; Beauchemin, A. M.; Xiao, W.-J. Angew. Chem. Int. Ed. 2014, 53, 12163. doi: 10.1002/anie.201406491
67. [67]
  Zhao, Q.-Q.; Zhou, X.-S.; Xu, S.-H.; Wu, Y.-L.; Xiao, W.-J.; Chen, J.-R. Org. Lett. 2020, 22, 2470. doi: 10.1021/acs.orglett.0c00712
68. [68]
  Zhang, X.; Huang, Q.-F.; Zou, W.-L.; Li, Q.-Z.; Feng, X.; Jia, Z.-Q.; Liu, Y.; Li, J.-L.; Wang, Q.-W. Org. Chem. Front. 2019, 6, 3321. doi: 10.1039/C9QO00509A
69. [69]
  Wang, Q.; Chang, H.; Wei, W.; Liu, Q.; Gao, W.; Li, Y.; Li, X. Chin. J. Org. Chem. 2016, 36, 939 (in Chinese).
70. [70]
  Chai, Z. Synthesis 2020, 52, 1738. doi: 10.1055/s-0039-1690857
71. [71]
  Ling, J.; Lam, S.; Low, K. H.; Chiu, P. Angew. Chem. Int. Ed. 2017, 56, 8879. doi: 10.1002/anie.201704155
72. [72]
  Moragas, T.; Liffey, R. M.; Regentova, D.; Ward, J. P.; Dutton, J.; Lewis, W.; Churcher, I.; Walton, L.; Souto, J. A.; Stockman, R. A. Angew. Chem., Int. Ed. 2016, 55, 10047. doi: 10.1002/anie.201604188
73. [73]
  Kaldas, S. J.; Kran, E.; Muck-Lichtenfeld, C.; Yudin, A. K.; Studer, A. Chem. Eur. J. 2020, 26, 1501. doi: 10.1002/chem.201904727
74. [74]
  Wu, A.; Feng, Q.; Sung, H. H. Y.; Williams, I. D.; Sun, J. Angew. Chem., Int. Ed. 2019, 58, 6776. doi: 10.1002/anie.201902866
1. [1]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
2. [2]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
3. [3]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
4. [4]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
5. [5]
  Xinghai Liu , Hongke Wu . Exploration and Practice of Ideological and Political Education in Heterocyclic Chemistry Based on "Fentanyl" Event. University Chemistry, 2024, 39(8): 359-364. doi: 10.3866/PKU.DXHX202312100
6. [6]
  Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
7. [7]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
8. [8]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
9. [9]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
10. [10]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
11. [11]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
12. [12]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
13. [13]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
14. [14]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
15. [15]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
16. [16]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
17. [17]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
18. [18]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
19. [19]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
20. [20]
  Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386

Get Citation

PDF

XML

Metrics

PDF Downloads(69)
Abstract views(4939)
HTML views(852)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142