Citation: Sai Zhang, Gaochen Xu, Huan Yan, Qinghuan Wu, Jingjing Meng, Jindian Duan, Kai Guo. Electrooxidative [3 + 2] annulation of amidines with alkenes for the synthesis of spiroimidazolines[J]. Chinese Chemical Letters, ;2022, 33(12): 5128-5131. doi: 10.1016/j.cclet.2022.04.006 shu

Electrooxidative [3 + 2] annulation of amidines with alkenes for the synthesis of spiroimidazolines

College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 211816, China

duanjd@njtech.edu.cn

guok@njtech.edu.cn

Received Date: 16 January 2022
Revised Date: 2 April 2022
Accepted Date: 3 April 2022
Available Online: 8 April 2022

Figures(7)

The electrooxidative [3 + 2] annulation of amidines with 2-arylideneindane-1,3-diones or 4-alkylidene pyrazolones is reported using NaI as a redox catalyst and electrolyte under constant current electrolysis in an undivided cell. The current strategy features excellent functional group tolerance, simple operation, and mild conditions, thus providing an environmentally benign and efficient access to spiroimidazolines in moderate to good yields.
- Electrooxidative,
- Amidines,
- Alkenes,
- Spiroimidazolines,
- Annulation
1. [1]
  D.C. Kombo, A.A. Mazurov, J. Chewning, et al., Bioorg. Med. Chem. Lett. 22 (2012) 1179–1186. doi: 10.1016/j.bmcl.2011.11.090
2. [2]
  A. Dekeyne, M.J. Millan, Neuropharmacology 51 (2006) 718–726. doi: 10.1016/j.neuropharm.2006.05.012
3. [3]
  C.A. Bernhart, P.M. Perreaut, B.P. Ferrari, et al., J. Med. Chem. 36 (1993) 3371–3380. doi: 10.1021/jm00074a018
4. [4]
  S. Kato, T. Yoshino, M. Shibasaki, M. Kanai, S. Matsunaga, Angew. Chem. Int. Ed. 51 (2012) 7007–7010. doi: 10.1002/anie.201203005
5. [5]
  H. Cai, Y. Zhou, D. Zhang, J. Xu, H. Liu, Chem. Commun. 50 (2014) 14771–14774. doi: 10.1039/C4CC06000H
6. [6]
  M. Zhao, L. Jing, H. Zhou, M. Shi, RSC Adv. 5 (2015) 75648–75652. doi: 10.1039/C5RA17075C
7. [7]
  J. Ren, C. Pi, X. Cui, Y. Wu, Org. Lett. 23 (2021) 6628–6632. doi: 10.1021/acs.orglett.1c02077
8. [8]
  H. Liang, G. Li, L. Zhang, et al., Org. Lett. 23 (2021) 5821–5825. doi: 10.1021/acs.orglett.1c01970
9. [9]
  Y. Zhang, J. Kuang, X. Xiao, L. Wang, Y. Ma, Org. Lett. 23 (2021) 3960–3964. doi: 10.1021/acs.orglett.1c01116
10. [10]
  W. Liu, J. He, X. Liu, et al., J. Org. Chem. 85 (2020) 14954–14962. doi: 10.1021/acs.joc.0c01715
11. [11]
  C. Wang, Y. Yu, Z. Su, X. Li, H. Cao, Org. Lett. 21 (2019) 4420–4423. doi: 10.1021/acs.orglett.9b00969
12. [12]
  W. Liu, Y. Zhang, J. He, et al., J. Org. Chem. 84 (2019) 11348–11358. doi: 10.1021/acs.joc.9b01818
13. [13]
  D. Meng, Y. Xie, Q. Peng, J. Wang, Org. Lett. 22 (2020) 7635–7639. doi: 10.1021/acs.orglett.0c02832
14. [14]
  J. Li, M. John, L. Ackermann, Chem. Eur. J. 20 (2014) 5403–5408. doi: 10.1002/chem.201304944
15. [15]
  A. Chaskar, S. Pardeshi, P. Sathe, K. Vadagaonkar, Adv. Synth. Catal. 359 (2017) 4217–4226. doi: 10.1002/adsc.201700900
16. [16]
  Y. Li, Y. Fu, C. Ren, et al., Org. Chem. Front. 2 (2015) 1632–1636. doi: 10.1039/C5QO00285K
17. [17]
  P. Wu, J. Qu, Y. Li, et al., Adv. Synth. Catal. 357 (2015) 3868–3874. doi: 10.1002/adsc.201500701
18. [18]
  D. Tang, P. Wu, X. Liu, et al., J. Org. Chem. 78 (2013) 2746–2750. doi: 10.1021/jo302555z
19. [19]
  X. Liu, D. Wang, Y. Chen, D. Tang, B. Chen, Adv. Synth. Catal. 355 (2013) 2798–2802. doi: 10.1002/adsc.201300590
20. [20]
  X. Liu, D. Wang, B. Chen, Tetrahedron 69 (2013) 9417–9421. doi: 10.1016/j.tet.2013.08.077
21. [21]
  Y. Zhu, C. Li, J. Zhang, et al., Org. Lett. 17 (2015) 3872–3875. doi: 10.1021/acs.orglett.5b01854
22. [22]
  Z. Zhan, M. Zhang, P. Jiang, et al., Asian J. Org. Chem. 10 (2021) 1801–1813. doi: 10.1002/ajoc.202100287
23. [23]
  H. Xu, R. Hong, M. Weng, et al., Org. Lett. 23 (2021) 5305–5310. doi: 10.1021/acs.orglett.1c01475
24. [24]
  H. Xu, R. Huang, Z. Shu, R. Hong, Z. Zhang, Org. Biomol. Chem. 19 (2021) 4978–4985. doi: 10.1039/d1ob00508a
25. [25]
  H. Xu, K. Chen, H. Liu, G. Wang, Org. Chem. Front. 5 (2018) 2864–2869. doi: 10.1039/c8qo00723c
26. [26]
  S. Tang, Y. Liu, A. Lei, Chem 4 (2018) 27–45. doi: 10.1016/j.chempr.2017.10.001
27. [27]
  Y. Yuan, A. Lei, Nat. Commun. 11 (2020) 802. doi: 10.1038/s41467-020-14322-z
28. [28]
  Z. Yang, Y. Yua, L. Lai, et al., Green Synth. Catal. 2 (2021) 19–26. doi: 10.1016/j.gresc.2021.01.009
29. [29]
  Y. Yuan, A. Lei, Acc. Chem. Res. 52 (2019) 3309–3324. doi: 10.1021/acs.accounts.9b00512
30. [30]
  J.C. Siu, N. Fu, S. Lin, Acc. Chem. Res. 53 (2020) 547–560. doi: 10.1021/acs.accounts.9b00529
31. [31]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319. doi: 10.1021/acs.chemrev.7b00397
32. [32]
  K. Jiao, Y. Xing, Q. Yang, H. Qiu, T. Mei, Acc. Chem. Res. 53 (2020) 300–310. doi: 10.1021/acs.accounts.9b00603
33. [33]
  R. Francke, R.D. Little, Chem. Soc. Rev. 43 (2014) 2492–2521. doi: 10.1039/c3cs60464k
34. [34]
  Y. Jiang, K. Xu, C. Zeng, Chem. Rev. 118 (2018) 4485–4540. doi: 10.1021/acs.chemrev.7b00271
35. [35]
  X. Chen, F. Xiao, W. He, Org. Chem. Front. 8 (2021) 5206–5228. doi: 10.1039/d1qo00375e
36. [36]
  C. Ma, P. Fang, Z. Liu, et al., Sci. Bull. 66 (2021) 2412–2429. doi: 10.1016/j.scib.2021.07.011
37. [37]
  J. Zhong, Y. Yu, D. Zhang, K. Ye, Chin. Chem. Lett. 32 (2021) 963–972. doi: 10.1016/j.cclet.2020.08.011
38. [38]
  Y. Yu, Y. Jiang, S. Wu, et al., Chin. Chem. Lett. 33 (2022) 2009–2014. doi: 10.1016/j.cclet.2021.10.016
39. [39]
  P. Xiong, H. Xu, Acc. Chem. Res. 52 (2019) 3339–3350. doi: 10.1021/acs.accounts.9b00472
40. [40]
  M.K. Kärkäs, Chem. Soc. Rev. 47 (2018) 5786–5865. doi: 10.1039/c7cs00619e
41. [41]
  C. Ma, P. Fang T. Mei, ACS Catal. 8 (2018) 7179–7189. doi: 10.1021/acscatal.8b01697
42. [42]
  T. Xiong, Q. Zhang, Chem. Soc. Rev. 45 (2016) 3069–3087. doi: 10.1039/C5CS00852B
43. [43]
  N. Dagar, P.P. Sen, S.R. Roy, ChemSusChem 14 (2021) 1229–1257. doi: 10.1002/cssc.202002567
44. [44]
  N. Chen, H. Xu, Green Synth. Catal. 2 (2021) 165–178. doi: 10.1016/j.gresc.2021.03.002
45. [45]
  Q. Yang, Y. Li, Y. Liu, et al., Org. Chem. Front. 8 (2021) 5410–5417. doi: 10.1039/d1qo00959a
46. [46]
  J. Chen, H. Wu, Q. Gui, et al., Org. Lett. 22 (2020) 2206–2209. doi: 10.1021/acs.orglett.0c00387
47. [47]
  C. Sun, F. Lian, K. Xu, C. Zeng, B. Sun, Adv. Synth. Catal. 361 (2019) 4041–4047. doi: 10.1002/adsc.201900537
48. [48]
  K. Liu, C. Song, J. Wu, et al., Green Chem. 21 (2019) 765–769. doi: 10.1039/c8gc03786h
49. [49]
  Z. Hou, Z. Mao, Y.Y. Melcamu, X. Lu, H. Xu, Angew. Chem. Int. Ed. 57 (2018) 1636–1639. doi: 10.1002/anie.201711876
50. [50]
  J.C. Siu, J.B. Parry, S. Lin, J. Am. Chem. Soc. 141 (2019) 2825–2831. doi: 10.1021/jacs.8b13192
51. [51]
  K. Hu, Y. Zhang, Z. Zhou, et al., Org. Lett. 22 (2020) 5773–5777. doi: 10.1021/acs.orglett.0c01821
52. [52]
  H. Wang, J. Shi, J. Tan, et al., Org. Lett. 21 (2019) 9430–9433. doi: 10.1021/acs.orglett.9b03641
53. [53]
  M. Zheng, X. Yuan, Y. Cui, et al., Org. Lett. 20 (2018) 7784–7789. doi: 10.1021/acs.orglett.8b03191
54. [54]
  C. Liu, Q. Jiang, Y. Lin, Z. Fang, K. Guo, Org. Lett. 22 (2020) 795–799. doi: 10.1021/acs.orglett.9b04141
55. [55]
  J. Duan, Y. Mao, L. Zhang, et al., Adv. Synth. Catal. 362 (2020) 695–699. doi: 10.1002/adsc.201901333
56. [56]
  Y. Wu, H. Yi, A. Lei, ACS Catal. 8 (2018) 1192–1196. doi: 10.1021/acscatal.7b04137
57. [57]
  Z. Ye, J. Gao, X. Duan, et al., Chem. Commun. 57 (2021) 8969–8972. doi: 10.1039/d1cc03288g
58. [58]
  X. Dong, R. Wang, W. Jin, C. Liu, Org. Lett. 22 (2020) 3062–3066. doi: 10.1021/acs.orglett.0c00814
59. [59]
  Y. Kurimoto, J. Yamashita, K. Mitsudo, E. Sato, S. Suga, Org. Lett. 23 (2021) 3120–3124. doi: 10.1021/acs.orglett.1c00807
60. [60]
  C. Cai, X. Shu, H. Xu, Nat. Commun. 10 (2019) 4953. doi: 10.1038/s41467-019-13024-5
61. [61]
  K. Hu, Y. Zhang, Z. Zhou, et al., Org. Lett. 22 (2020) 5773–5777. doi: 10.1021/acs.orglett.0c01821
1. [1]
  Xiaojian Ren , Qiang Liu , Zhixiang Wang , Xiangyu Chen . Visible-light-induced direct hydrodifluoromethylation of alkenes with difluoromethyltriphenylphosphonium iodide salt. Chinese Chemical Letters, 2023, 34(1): 107473-1-107473-4. doi: 10.1016/j.cclet.2022.04.071
2. [2]
  Wang Guodong , Guo Yanhui , Wan Jieping . Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines. Chinese Journal of Organic Chemistry, 2020, 40(3): 645-650. doi: 10.6023/cjoc201912018
3. [3]
  Changwei Chen , Sunliang Cui . BF₃-promoted annulation of azonaphthalenes and ynamides for synthesis of benzo[e]indoles. Chinese Chemical Letters, 2021, 32(1): 421-424. doi: 10.1016/j.cclet.2020.04.010
4. [4]
  Ping Zhang , Wenju Chang , Hongyun Jiao , Yanshang Kang , Wenxuan Zhao , Peipei Cui , Yong Liang , Wei-Yin Sun , Yi Lu . Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst. Chinese Chemical Letters, 2021, 32(5): 1717-1720. doi: 10.1016/j.cclet.2021.01.024
5. [5]
  Deping Wang , Yan Liu , Linhua Wang , Hu Cheng , Yuming Zhang , Ge Gao . Synthesis of π-extended dibenzo[d, k]ullazines by a palladium-catalyzed double annulation using arynes. Chinese Chemical Letters, 2021, 32(4): 1407-1410. doi: 10.1016/j.cclet.2020.09.057
6. [6]
  Yuncan Chen , Shan Lv , Ruizhi Lai , Yingying Xu , Xin Huang , Jianglian Li , Guanghui Lv , Yong Wu . Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas. Chinese Chemical Letters, 2021, 32(8): 2555-2558. doi: 10.1016/j.cclet.2021.02.052
7. [7]
  Liqiang Hao , Hongyan Liu , Zheng Zhang , Fuqiang Wen , Chengcai Xia , Zengfen Pang . Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1, 2-dichloroethane. Chinese Chemical Letters, 2021, 32(7): 2309-2312. doi: 10.1016/j.cclet.2021.02.025
8. [8]
  Yanhui Guo , Yunyun Liu , Jie-Ping Wan . Amine-catalyzed synthesis of N²-sulfonyl 1, 2, 3-triazole in water and the tunable N²-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation. Chinese Chemical Letters, 2022, 33(2): 855-858. doi: 10.1016/j.cclet.2021.08.003
9. [9]
  Cao Weidi , Liu Xiaohua , Feng Xiaoming . Chiral organobases: Properties and applications in asymmetric catalysis. Chinese Chemical Letters, 2018, 29(8): 1201-1208. doi: 10.1016/j.cclet.2018.05.041
10. [10]
  Zhi-Wei Chen , Jun-Bo Hou , Zhao-Ran Dai , Xiao-Feng Yang . A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation. Chinese Chemical Letters, 2016, 27(10): 1622-1625. doi: 10.1016/j.cclet.2016.04.009
11. [11]
  Li Yao , Chen Kunquan , Zhang Yan , Sun Dequn , Ye Song . N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones. Chinese Chemical Letters, 2018, 29(8): 1209-1211. doi: 10.1016/j.cclet.2018.03.003
12. [12]
  Han Xiang-Lei , Lin Peng-Peng , Li Qingjiang . Recent advances of allenes in the first-row transition metals catalyzed C—H activation reactions. Chinese Chemical Letters, 2019, 30(8): 1495-1502. doi: 10.1016/j.cclet.2019.04.027
13. [13]
  Hui Zheng , Ying Han , Jing Sun , Chao-Guo Yan . Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate. Chinese Chemical Letters, 2021, 32(5): 1683-1686. doi: 10.1016/j.cclet.2020.12.024
14. [14]
  Song Zou , Zeyu Zhang , Chao Chen , Chanjuan Xi . MeOTf-catalyzed formal [4 + 2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion. Chinese Chemical Letters, 2022, 33(6): 3021-3025. doi: 10.1016/j.cclet.2021.12.012
15. [15]
  Shoudong Xie , Weinan Chen , Si Liu , Hao Zong , Binbin Ming , Gang Zhou . Facile synthesis and functionalization of fluoranthenes via intramolecular [4 + 2] annulations between thiophenes and alkynes. Chinese Chemical Letters, 2023, 34(6): 107642-1-107642-4. doi: 10.1016/j.cclet.2022.06.065
16. [16]
  He Juan . The History of the Chinese Chemical Terms Wan, Xi and Que. Chemistry, 2016, 79(7): 667-670,666.
17. [17]
  Xukai Zhou , Jiaqiong Sun , Xingwei Li . Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control. Chinese Journal of Catalysis, 2018, 39(11): 1782-1791. doi: 10.1016/S1872-2067(18)63134-1
18. [18]
  WANG Zhen , LI En , HE Zhiqi , CHEN Jiean , HUANG Yong . Dehydrogenative Annulation of γ, δ-Unsaturated Amides and Alkynes via Double C―H Activation. Acta Physico-Chimica Sinica, 2019, 35(9): 906-912. doi: 10.3866/PKU.WHXB201811038
19. [19]
  Yun Fa Zheng , Jian Yu , Guo Bing Yan , Xu Li , Song Luo . FeBr₃-catalyzed dibromination of alkenes and alkynes. Chinese Chemical Letters, 2011, 22(10): 1195-1198. doi: 10.1016/j.cclet.2011.05.005
20. [20]
  Wei Yuan HUANG , Han Zhong ZHNG . ORGANOPHOSPHINE INITIATED REACTION OF PERFLUOROALKYL IODIDES WITH ALKENES. Chinese Chemical Letters, 1990, 1(2): 153-154.

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(166)
HTML views(1)

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