Citation: Hao Yongjia, Gong Yi, Cao Zhongyan, Zhou Ying, Zhou Jian. A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1, 4-di-thiane-2, 5-diol[J]. Chinese Chemical Letters, ;2020, 31(3): 681-684. doi: 10.1016/j.cclet.2019.08.018 shu

A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1, 4-di-thiane-2, 5-diol

Hao Yongjia ^a ,
Gong Yi ^b ,
Cao Zhongyan ^b ,
Zhou Ying ^a,*, ,
Zhou Jian ^b,*,

a.
School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China
b.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China

yingzhou71@126.com

jzhou@chem.ecnu.edu.cn

Received Date: 29 May 2019
Revised Date: 23 July 2019
Accepted Date: 14 August 2019
Available Online: 16 August 2019

Figures(4)

Spirooxindoles play an important role in drug discovery and development. The development of efficient methods for the synthesis of spirooxindoles from easily available starting materials is of current interest. Herein, we report in detail the In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles and 1, 4-di-thiane-2, 5-diol, which allows the facile preparation of spiro[indoline-3, 4'-thiopyran]-2-ones bearing (tetrahydro)thiopyran skeleton.
- Spirooxindoles,
- Lewis acid catalysis,
- [3 + 3] cycloaddition,
- Sulfur heterocycles,
- Cyclopropane
1. [1]
  C.V. Galliford, K.A. Scheidt, Angew. Chem. Int. Ed. 46 (2007) 8748-8758. doi: 10.1002/anie.200701342
2. [2]
  H. Lin, S.J. Danishefsky, Angew. Chem. Int. Ed. 42 (2003) 36-51. doi: 10.1002/anie.200390048
3. [3]
  C. Marti, E.M. Carreira, Eur. J. Org. Chem. (2003) 2209-2219.
4. [4]
  B.M. Trost, M.K. Brennan, Synthesis (2009) 3003-3025.
5. [5]
  S. Peddibhotla, Curr. Bioact. Compd. 5 (2009) 20-38. doi: 10.2174/157340709787580900
6. [6]
  N. Ye, H. Chen, E.A. Wold, P.D. Shi, J. Zhou, ACS Infect. Dis. 2 (2016) 382-392. doi: 10.1021/acsinfecdis.6b00041
7. [7]
  E.M. Carreira, T.C. Fessard, Chem. Rev. 114 (2014) 8257-8322. doi: 10.1021/cr500127b
8. [8]
  J.H. Xie, Q.L. Zhou, Acta Chim. Sin. 72 (2014) 778-797. doi: 10.6023/A14050364
9. [9]
  A.S. Ding, M. Meazza, H. Guo, J.W. Yang, R. Rios, Chem. Soc. Rev. 47 (2018) 5946-5996. doi: 10.1039/C6CS00825A
10. [10]
  Z.Y. Cao, F. Zhou, J. Zhou, Acc. Chem. Res. 51 (2018) 1443-1454. doi: 10.1021/acs.accounts.8b00097
11. [11]
  F. Zhou, Y.L. Liu, J. Zhou, Adv. Synth. Catal. 352 (2010) 1381-1407. doi: 10.1002/adsc.201000161
12. [12]
  H. Wang, R. Wang, Adv. Synth. Catal. 355 (2013) 1023-1052. doi: 10.1002/adsc.201200808
13. [13]
  N.R. Ball-Jones, J.J. Badillo, A.K. Franz, Org. Biomol. Chem.10 (2012) 5165-5181. doi: 10.1039/c2ob25184a
14. [14]
  D.J. Cheng, Y. Ishihara, B. Tan, C.F. Barbas III, ACS Catal. 4 (2014) 743-762. doi: 10.1021/cs401172r
15. [15]
  M. Meazza, R. Rios, Chem. -Eur. J. 22 (2016) 9923-9928. doi: 10.1002/chem.201601893
16. [16]
  J. Yang, X.W. Liu, D.D. Wang, et al., Tetrahedron 72 (2016) 8523-8536. doi: 10.1016/j.tet.2016.10.050
17. [17]
  K. Parthasarathy, C. Praveen, J.C. Jeyaveeran, A.A.M. Prince, Bioorg. Med. Chem. Lett. 24 (2016) 4310-4317. doi: 10.1016/j.bmc.2016.07.022
18. [18]
  S.D. Lotesta, A.P. Marcus, Y.J. Zheng, et al., Bioorg. Med. Chem. 24 (2016) 1384-1391. doi: 10.1016/j.bmc.2016.02.014
19. [19]
  Y. Arun, K. Saranraj, C. Balachandran, P.T. Perumal, Eur. J. Med. Chem. 74 (2014) 50-64. doi: 10.1016/j.ejmech.2013.12.027
20. [20]
  S. Haddad, S. Boudriga, T.N. Akhaja, et al., New J. Chem. 39 (2015) 520-528. doi: 10.1039/C4NJ01008F
21. [21]
  M. Gicquel, C. Gomez, M.C.G.A. lvarez, et al., J. Med. Chem. 61 (2018) 9386-9392. doi: 10.1021/acs.jmedchem.8b01137
22. [22]
  M.H. Feng, B. Tang, S.H. Liang, X.F. Jiang, Curr. Top. Med. Chem.16 (2016) 1200-1216. doi: 10.2174/1568026615666150915111741
23. [23]
  J.S. Yu, H.M. Huang, P.G. Ding, et al., ACS Catal. 6 (2016) 5319-5344. doi: 10.1021/acscatal.6b01496
24. [24]
  P. Chauhan, S. Mahajan, D. Enders, Chem. Rev. 114 (2014) 8807-8864. doi: 10.1021/cr500235v
25. [25]
  B.R. Beno, K.S. Yeung, M.D. Bartberger, L.D. Pennington, N.A. Meanwell, J. Med. Chem. 58 (2015) 4383-4438. doi: 10.1021/jm501853m
26. [26]
  P. Przybylski, K. Pyta-Klich, K. Pyta, A. Janas, Tetrahedron 74 (2018) 6335-6365. doi: 10.1016/j.tet.2018.09.022
27. [27]
  M.H. Qureshi, D.T. Smith, M.D. Delost, J.T. Njarðarson, Top 200 Pharmaceutical Products by Prescriptions in 2016, (2018). (accessed Oct., 2018) https://njardarson.lab.arizona.edu/sites/njardarson.lab.arizona.edu/files/2016Top200PharmaceuticalPrescriptionSalesPosterLowResV2.pdf.
28. [28]
  P. Eastwood, J. González, E. Gómez, et al., Bioorg. Med. Chem. Lett. 21 (2011) 5270-5273. doi: 10.1016/j.bmcl.2011.07.033
29. [29]
  A. Bertamino, M. Soprano, S. Musella, et al., J. Med. Chem. 56 (2013) 5407-5421. doi: 10.1021/jm400311n
30. [30]
  V. Vintonyak, K. Warburg, H. Kruse, et al., Angew. Chem. Int. Ed. 49 (2010) 5902-5905. doi: 10.1002/anie.201002138
31. [31]
  S.Z. Wang, Y. Jiang, S.C. Wu, et al., Org. Lett. 18 (2016) 1028-1031. doi: 10.1021/acs.orglett.6b00155
32. [32]
  S. Duan, Y. Li, Y.Y. Liu, et al., Chem. Commun. 48 (2012) 5160-5162. doi: 10.1039/c2cc30931a
33. [33]
  Y.M. Huang, C.W. Zheng, Z. Chai, G. Zhao, Adv. Synth. Catal. 356 (2014) 579-583. doi: 10.1002/adsc.201300833
34. [34]
  P.F. Zhou, Y.F. Cai, L.L. Lin, et al., Adv. Synth. Catal. 357 (2015) 695-700. doi: 10.1002/adsc.201400964
35. [35]
  P. Cheng, W.G. Guo, P. Chen, et al., Chem. Commun. 52 (2016) 3418-3421. doi: 10.1039/C5CC10292H
36. [36]
  B.X. Feng, J.D. Yang, J. Li, X. Li, Tetrahedron Lett. 57 (2016) 3457-3461. doi: 10.1016/j.tetlet.2016.06.084
37. [37]
  Y.Y. Gui, J. Yang, L.W. Qi, et al., Org. Biomol. Chem. 13 (2015) 6371-6379. doi: 10.1039/C5OB00774G
38. [38]
  G.L. Xiao, T.T. Chen, C.Q. Ma, D. Xing, W.H. Hu, Org. Lett. 20 (2018) 4531-4535. doi: 10.1021/acs.orglett.8b01833
39. [39]
  S.V. Kumar, P. Prasanna, S. Perumal, Tetrahedron Lett. 54 (2013) 6651-6655. doi: 10.1016/j.tetlet.2013.09.123
40. [40]
  S.Z. Wang, Z.J. Guo, S.Q. Chen, et al., Chem. -Eur. J. 24 (2018) 62-66. doi: 10.1002/chem.201703837
41. [41]
  S.Z. Wang, S.Q. Chen, Z.J. Guo, et al., Org. Biomol. Chem. 16 (2018) 625-634. doi: 10.1039/C7OB02726E
42. [42]
  T. Arai, T. Miyazaki, H. Ogawa, H. Masu, Org. Lett. 18 (2016) 5824-5827. doi: 10.1021/acs.orglett.6b02783
43. [43]
  Z. Sun, S.S. Tian, S.L. Li, et al., Tetrahedron Lett. 58 (2017) 3401-3405. doi: 10.1016/j.tetlet.2017.07.033
44. [44]
  H.K. Grover, M.R. Emmett, M.A. Kerr, Org. Biomol. Chem. 13 (2015) 655-671. doi: 10.1039/C4OB02117G
45. [45]
  T.F. Schneider, J.Kaschel, D.B. Werz, Angew. Chem.Int.Ed.53 (2014) 5504-5523. doi: 10.1002/anie.201309886
46. [46]
  (a) S. Liao, X.L. Sun, Y. Tang, Acc. Chem. Res. 47 (2014) 2260-2272;
  (b) G. Sathishkannan, K. Srinivasan, Chem. Commun. 50 (2014) 4062-4064;
  (c) X. Fang, J. Li, H.Y. Tao, C.J. Wang, Org. Lett. 15 (2013) 5554-5557.
47. [47]
  Z.Y. Cao, J. Zhou, Org. Chem. Front. 2 (2015) 849-858. doi: 10.1039/C5QO00092K
48. [48]
  Z.Y. Cao, X.M. Wang, C. Tan, et al., J. Am. Chem. Soc. 135 (2013) 8197-8200. doi: 10.1021/ja4040895
49. [49]
  P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, E.M. Carreira, Angew. Chem. Int. Ed. 38 (1999) 3186-3189. doi: 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO;2-E
50. [50]
  P.W. Xu, J. Liu, L. Shen, et al., Nat. Commun. 8 (2017) 1619. doi: 10.1038/s41467-017-01451-1
51. [51]
  F.M. Liao, Z.Y. Cao, J.S. Yu, J. Zhou, Angew. Chem. Int. Ed. 56 (2017) 2459-2463. doi: 10.1002/anie.201611625
52. [52]
  J.S. Yu, F.M. Liao, W.M. Gao, et al., Angew. Chem. Int. Ed. 54 (2015) 7381-7385. doi: 10.1002/anie.201501747
53. [53]
  X.P. Yin, X.P. Zeng, Y.L. Liu, et al., Angew. Chem. Int. Ed. 53 (2014) 13740-13745. doi: 10.1002/anie.201407677
54. [54]
  F. Zamberlan, A. Fantinati, C. Trapella, Eur. J. Org. Chem. (2018) 3248-3264.
55. [55]
  H.P. Wang, H.H. Zhang, X.Q. Hu, P.F. Xu, Y.C. Luo, Eur. J. Org. Chem. (2015) 3486-3494.
56. [56]
  X. Fu, L.L. Lin, Y. Xia, et al., Org. Biomol. Chem. 14 (2016) 5914-5917. doi: 10.1039/C6OB00948D
57. [57]
  R.K. Varshanya, P. Banerjee, Org. Biomol. Chem. 15 (2017) 5182-5190. doi: 10.1039/C7OB00941K
1. [1]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
2. [2]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
3. [3]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
4. [4]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
5. [5]
  Yan Wang , Huixin Chen , Fuda Yu , Shanyue Wei , Jinhui Song , Qianfeng He , Yiming Xie , Miaoliang Huang , Canzhong Lu . Oxygen self-doping pyrolyzed polyacrylic acid as sulfur host with physical/chemical adsorption dual function for lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(7): 109001-. doi: 10.1016/j.cclet.2023.109001
6. [6]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
7. [7]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
8. [8]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
9. [9]
  Xun Zhu , Chenchen Zhang , Yingying Li , Yin Lu , Na Huang , Dawei Wang . Degradation of perfluorooctanoic acid by inductively heated Fenton-like process over the Fe₃O₄/MIL-101 composite. Chinese Chemical Letters, 2024, 35(12): 109753-. doi: 10.1016/j.cclet.2024.109753
10. [10]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
11. [11]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
12. [12]
  Jun Jiang , Tong Guo , Wuxin Bai , Mingliang Liu , Shujun Liu , Zhijie Qi , Jingwen Sun , Shugang Pan , Aleksandr L. Vasiliev , Zhiyuan Ma , Xin Wang , Junwu Zhu , Yongsheng Fu . Modularized sulfur storage achieved by 100% space utilization host for high performance lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(4): 108565-. doi: 10.1016/j.cclet.2023.108565
13. [13]
  Feng Cao , Chunxiang Xian , Tianqi Yang , Yue Zhang , Haifeng Chen , Xinping He , Xukun Qian , Shenghui Shen , Yang Xia , Wenkui Zhang , Xinhui Xia . Gelation-pyrolysis strategy for fabrication of advanced carbon/sulfur cathodes for lithium-sulfur batteries. Chinese Chemical Letters, 2025, 36(3): 110575-. doi: 10.1016/j.cclet.2024.110575
14. [14]
  Gregorio F. Ortiz . Some facets of the Mg/Na₃VCr_0.5Fe_0.5(PO₄)₃ battery. Chinese Chemical Letters, 2024, 35(10): 109391-. doi: 10.1016/j.cclet.2023.109391
15. [15]
  Ruike Hu , Kangmin Wang , Junxiang Liu , Jingxian Zhang , Guoliang Yang , Liqiu Wan , Bijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113
16. [16]
  Yan ZHAO , Jiaxu WANG , Zhonghu LI , Changli LIU , Xingsheng ZHAO , Hengwei ZHOU , Xiaokang JIANG . Gd³⁺-doped Sc₂W3O₁₂: Eu³⁺ red phosphor: Preparation and luminescence performance. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 461-468. doi: 10.11862/CJIC.20240316
17. [17]
  Fangling Cui , Zongjie Hu , Jiayu Huang , Xiaoju Li , Ruihu Wang . MXene-based materials for separator modification of lithium-sulfur batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100337-100337. doi: 10.1016/j.cjsc.2024.100337
18. [18]
  Minjun Yin , Yuhui Lin , Manli Zhuang , Wei Xiao , Jie Wu . Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide. Chinese Chemical Letters, 2025, 36(3): 109926-. doi: 10.1016/j.cclet.2024.109926
19. [19]
  Jiayi Guo , Liangxiong Ling , Qinwei Lu , Yi Zhou , Xubiao Luo , Yanbo Zhou . Degradation of chloroxylenol by CoS_x activated peroxomonosulfate: Role of cobalt-sulfur ratio. Chinese Chemical Letters, 2025, 36(4): 110380-. doi: 10.1016/j.cclet.2024.110380
20. [20]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(772)
HTML views(7)

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

A highly efficient In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1, 4-di-thiane-2, 5-diol

Metrics

通讯作者: 陈斌, bchen63@163.com

A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1, 4-di-thiane-2, 5-diol