Citation: Guo Xin, Guo Yajun, Kong Dezhi, Lu Huijie, Hua Yuanzhao, Wang Mincan. Efficient Synthesis of Tetrahydrofuran Spirooxindoles via One-Pot Reaction[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1999-2007. doi: 10.6023/cjoc202003029 shu

Efficient Synthesis of Tetrahydrofuran Spirooxindoles via One-Pot Reaction

  • Corresponding author: Hua Yuanzhao, hyzhao@zzu.edu.cn Wang Mincan, wangmincan@zzu.edu.cn
  • Received Date: 11 March 2020
    Revised Date: 20 April 2020

    Fund Project: Education Department of Henan Province 17B150014Education Department of Henan Province 18B150028National Natural Science Foundation of China 21272216the China Postdoctoral Science Foundation 2017M622361National Natural Science Foundation of China (No. 21871237), the China Postdoctoral Science Foundation (No: 2017M622361) and the Education Department of Henan Province (Nos. 17B150014, 18B150028).

Figures(3)

  • A one-pot reaction of Michael/hemiketalization and Fridel-Crafts reaction of α-hydroxy aryl ketones and β, γ-unsaturated α-ketoamides has been developed. The process enables efficient synthesis of tetrahydrofuran spirooxindoles using chain substrates that do not contain oxindole and tetrahydrofuran skeletons. A spiro-carbon center, an oxindole ring and a tetrahydrofuran ring, are constructed in this process.
  • 加载中
    1. [1]

      (a) Rottmann, M.; McNamara, C.; Yeung, B. K. S.; Lee, M. C. S.; Zou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; Gonzalez-Paez, G. E.; Lakshminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H. P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Science 2010, 329, 1175.
      (b) Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104.
      (c) Zheng, Y. J.; Tice, C. M.; Singh, S. B. Bioorg. Med. Chem. Lett. 2014, 24, 3673.
      (d) Yu, B.; Yu, D. Q.; Liu, H. M. Eur. J. Med. Chem. 2015, 97, 673.
      (e) Ye, N.; Chen, H.; Wold, E. A.; Shi, P.-Y.; Zhou, J. ACS Infect. Dis. 2016, 2, 382.
      (f) Mei, G. J.; Shi, F. Chem. Commun. 2018, 54, 6607.

    2. [2]

      (a) Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20.
      (b) Cui, B.-D.; Zuo, J.; Zhao, J.-Q.; Zhou, M.-Q.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2014, 79, 5305.

    3. [3]

      ( a) Vintonyak, V. V.; Warburg, K.; Kruse, H.; Grimme, S.; Hübel, K.; Rauh, D.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 5902.
      (b) Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328.
      (c) Crosignani, S.; Jorand-Lebrun, C.; Page, P.; Campbell, G.; Colovray, V.; Missotten, M.; Humbert, Y.; Cleva, C.; Arrighi, J.-F.; Gaudet, M.; Johnson, Z.; Ferro, P.; Chollet, A. ACS Med. Chem. Lett. 2011, 2, 644.
      (d) Rana, S.; Natarajan, A. Org. Biomol. Chem. 2013, 11, 244.

    4. [4]

      Franz, A. K.; Dreyfuss, P. D.; Schreiber, S. L. J. Am. Chem. Soc. 2007, 129, 1020.  doi: 10.1021/ja067552n

    5. [5]

      Ghosh, A.; Carter, R. G. Angew. Chem., Int. Ed. 2019, 58, 681.  doi: 10.1002/anie.201807509

    6. [6]

      (a) Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2006, 71, 2346.
      (b) Li, J.; Liu, Y. J.; Li, C. J.; Jia, X. Chem.-Eur. J. 2011, 17, 7409.
      (c) Hanhan, N. V.; Jones, N. R.; Tran, N. T.; Franz, A. K. Angew. Chem., Int. Ed. 2012, 51, 989.
      (d) Yang, L.; Xie, P.; Li, E.; Li, X.; Huang, Y.; Chen, R. Org. Biomol. Chem. 2012, 10, 7628.
      (e) Lian, Z.; Shi, M. Eur. J. Org. Chem. 2012, 2012, 581.
      (f) Mei, L.-Y.; Wei, Y.; Xu, Q.; Shi, M. Organometallics 2013, 32, 3544.
      (g) Tang, Z.; Liu, Z.; An, Y.; Jiang, R.; Zhang, X.; Li, C.; Jia, X.; Li, J. J. Org. Chem. 2016, 81, 9158.
      (h) Silvi, M.; Chatterjee, I.; Liu, Y.-K.; Melchiorre, P. Angew. Chem., Int. Ed. 2013, 52, 10780.
      (i) Zhao, B.-L.; Du, D.-M. Adv. Synth. Catal. 2016, 358, 3992.
      (j) Zhu, Y.-S.; Wang, W.-B.; Yuan, B.-B.; Li, Y.-N.; Wang, Q.-L.; Bu, Z.-W. Org. Biomol. Chem. 2017, 15, 984.
      (k) Zhang, J.-H.; Wang, R.-B.; Li, D.-F.; Zhao, L.-M. ACS Omega 2017, 2, 7022.

    7. [7]

      (a) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
      (b) Jones, K.; Wilkinson, J. Chem. Commun. 1992, 1767.
      (c) Overman, L. E.; Rosen, M. D. Angew. Chem., Int. Ed. 2000, 39, 4596.
      (d) Kyei, A. S.; Tchabanenko, K.; Baldwin, J. E.; Adlington, R. M. Tetrahedron Lett. 2004, 45, 8931.
      (e) Jaegli, S.; Dufour, J.; Wei, H.-L.; Piou, T.; Duan, X.-H.; Vors, J.-P.; Neuville, L.; Zhu, J.-P. Org. Lett. 2010, 12, 4498.
      (f) Yin, B.-L.; Lai, J.-Q.; Zhang, Z.-R.; Jiang, H.-F. Adv. Synth. Catal. 2011, 353, 1961.

    8. [8]

    9. [9]

      (a) Song, X.; Liu, J.; Liu, M.-M.; Wang, X.; Zhang, Z.-F.; Wang, M.-C.; Chang, J. Tetrahedron 2014, 70, 5468.
      (b) Hua, Y.-Z.; Liu, M.-M.; Huang, P.-J.; Song, X.; Wang, M.-C.; Chang, J.-B. Chem.-Eur. J. 2015, 21, 11994.
      (c) Tao, B.-K.; Yang, H.; Hua, Y.-Z.; Wang, M.-C. Org. Biomol. Chem. 2019, 17, 4301.
      (d) Miao, Y.-H.; Hua, Y.-Z.; Wang, M.-C. Org. Biomol. Chem. 2019, 17, 7172.
      (e) Liu, M.-M.; Yang, X.-C.; Hua, Y.-Z.; Chang, J.-B.; Wang, M.-C. Org. Lett. 2019, 21, 7089.
      (f) Yi, Y.; Hua, Y.-Z.; Lu, H.-J.; Liu, L.-T.; Wang, M.-C. Org. Lett. 2020, 22, 2527.
      (g) Liu, M.-M.; Yang, X.-C.; Hua, Y.-Z.; Chang, J.-B.; Wang, M.-C. Org. Lett. 2019, 21, 2111.
      (h) Yang, X.-C.; Liu, M.-M.; Mathey, F.; Yang, H.; Hua, Y.-Z.; Wang, M.-C. J. Org. Chem. 2019, 84, 7762.

    10. [10]

      Guo, Y.-J.; Guo, X.; Kong, D.-Z.; Lu, H.-J.; Liu, L.-T.; Hua, Y.-Z.; Wang, M.-C. J. Org. Chem., 2020, 85, 4195. The minor diastereomers in this article are obtained in 23%~44% isolated yields with about 1:1dr value in the current study.  doi: 10.1021/acs.joc.9b03378

    11. [11]

      CCDC 1987133(5') contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre.

  • 加载中
    1. [1]

      Lei Zhang , Kaimin Chen , Luchang Li , Xiu Wei , Xianxin Cai , Yaohui Yu , Yixian Yang , Renping Cao , Fenghua Wei , Bang Lan , Yanhua Li , Xiaohu Luo , Hui Liang , Deshuai Zhen . One-pot synthesis of Ni–Co nanoparticles@Ni0.19Co0.26P nanowires core/shell arrays on Ni foam for efficient hydrogen evolution reaction at all pH values. Chinese Chemical Letters, 2026, 37(6): 111002-. doi: 10.1016/j.cclet.2025.111002

    2. [2]

      Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143

    3. [3]

      Min Fu , Ruihan Wang , Wenqiang Liu , Sen Zhou , Chunhong Zhong , Yaohao Li , Pan He , Xin Li , Shiying Shang , Zhongping Tan . Improved one-pot protein synthesis enabled by a more precise assessment of peptide arylthioester reactivity. Chinese Chemical Letters, 2025, 36(7): 110542-. doi: 10.1016/j.cclet.2024.110542

    4. [4]

      Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994

    5. [5]

      Jun-Gang Wang , Bing-Yi Zhou , Yao-Luo Hu , Yong-Dong Du , Rong-He Wu , Chun-Yan Wu , Wen-Chao Yang , An-Xin Wu . Atom-swapping skeletal editing of benzo[c]oxepines for the construction of 2-benzodiazepines via a continuous manufacturing one-pot synthesis. Chinese Chemical Letters, 2026, 37(4): 111200-. doi: 10.1016/j.cclet.2025.111200

    6. [6]

      Yufeng Gan , Deqian Zeng , Shunyan Ning , Ningchao Zheng , Xinpeng Wang , Yuezhou Wei , Jizhou Jiang . Synergistic H2 production and tetracycline degradation: Unveiling the mechanism of a one-pot synthesized CeO2/CdS photocatalyst. Chinese Chemical Letters, 2026, 37(5): 111717-. doi: 10.1016/j.cclet.2025.111717

    7. [7]

      Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575

    8. [8]

      Chun-Ying Xu , Xiao-Lin Luan , Yuan-Yuan Cui , Cheng-Xiong Yang . One-pot in situ doping synthesis of phenylboronic acid-functionalized magnetic-cyclodextrin microporous organic network for specific enrichment and detection of sulfonylurea herbicides. Chinese Chemical Letters, 2025, 36(9): 110937-. doi: 10.1016/j.cclet.2025.110937

    9. [9]

      Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028

    10. [10]

      Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012

    11. [11]

      Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880

    12. [12]

      Jun Huang , Jiangping Qin , Caijin Ban , Jingmei Yuan , Jing Yang , Guoping Yang . Visible-light induced cascade sulfonation/cyclization reaction in water towards sulfonated dihydroisoquinolino[1,2-b]quinazolinones. Chinese Chemical Letters, 2026, 37(2): 111379-. doi: 10.1016/j.cclet.2025.111379

    13. [13]

      Guangping Sun , Menglian Hu , Lujie Wu , Danping Zhu , Weixuan Ji , Yan Sun , Menghang Li , Jinli Zhu , Yanfeng Tang , Yong Yao . Three-step cascade artificial light-harvesting system for photooxidation reaction based on cation-pillar[5]arene. Chinese Chemical Letters, 2026, 37(9): 112190-. doi: 10.1016/j.cclet.2025.112190

    14. [14]

      Jun Shi , Xueting Zhou , Bing-Qing Yang , Biaobiao Jiang , Wei Wu , Hai Ren . Single-electron transfer enables enantioselective synthesis of spirooxindoles via dual copper and phosphoric acid catalysis. Chinese Chemical Letters, 2026, 37(4): 111250-. doi: 10.1016/j.cclet.2025.111250

    15. [15]

      Li-Hong Xiong , Liang Chen , Zhi-Tao He . Stereoselective in situ assembled hydrofunctionalization and cascade. Chinese Chemical Letters, 2026, 37(3): 111921-. doi: 10.1016/j.cclet.2025.111921

    16. [16]

      Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896

    17. [17]

      Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870

    18. [18]

      Qingshuang Xu ,  Libin Zeng . Cascade electrocatalysis enabled by interfacial microenvironment for sustainable hydroxylamine synthesis. Chinese Journal of Structural Chemistry, 2026, 45(2): 100799-100799. doi: 10.1016/j.cjsc.2025.100799

    19. [19]

      Hao Zhou , Xu-Dong Wang , Yu-Fei Ao , De-Xian Wang , Qi-Qiang Wang . Inherently chiral molecular barrels via directional cascade hooping. Chinese Chemical Letters, 2026, 37(5): 111443-. doi: 10.1016/j.cclet.2025.111443

    20. [20]

      Jie Yu , Jiuying Liao , Yan Zhao , Yu Liu . Hierarchical confinement achieving cascade phosphorescence resonance energy transfer and application. Chinese Chemical Letters, 2026, 37(7): 111964-. doi: 10.1016/j.cclet.2025.111964

Metrics
  • PDF Downloads(8)
  • Abstract views(1955)
  • HTML views(254)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return