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

Institute of Green Catalysis, College of Chemistry, Zhengzhou University, Zhengzhou 450000

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.
- one-pot,
- cascade reaction,
- tetrahydrofuran spirooxindoles
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.
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