Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Efficient Method for Multicomponent Synthesis of Spiro[4H-pyran-oxindole] Derivatives Catalyzed by Magnesium Perchlorate

  • Wu, Chunlei (Department of Chemistry and Chemical Engineering, Shaoxing University) ;
  • Shen, Runpu (Department of Chemistry and Chemical Engineering, Shaoxing University) ;
  • Chen, Jianhui (Department of Chemistry and Chemical Engineering, Shaoxing University) ;
  • Hu, Chunqi (Department of Chemistry and Chemical Engineering, Shaoxing University)
  • Received : 2013.01.31
  • Accepted : 2013.05.22
  • Published : 2013.08.20
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Abstract

A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described.

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References

  1. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970; p 56.
  2. Galliford, C. V.; Scheidt, K. A. Angew. Chem. Int. Ed. 2007, 46, 8748-8758. https://doi.org/10.1002/anie.200701342
  3. Deppermann, N.; Thomanek, H.; Maison, W.; Prenzel, A. J. Org. Chem. 2010, 75, 5994. https://doi.org/10.1021/jo101401z
  4. Kang, T. H.; Matsumoto, K.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Eur. J. Pharmacol. 2002, 444, 39. https://doi.org/10.1016/S0014-2999(02)01608-4
  5. Dandia, A.; Jain, A. K.; Bhati, D. S. Synth. Commun. 2011, 41, 2905. https://doi.org/10.1080/00397911.2010.515365
  6. Kidwai, M.; Jahan, A.; Mishra, N. K. Appl. Catal. A 2012, 35, 425.
  7. Wang, L. M.; Jiao, N.; Qiu, J.; Yu, J. J.; Liu, J. Q.; Guo, F. L. Tetrahedron 2010, 66, 339. https://doi.org/10.1016/j.tet.2009.10.091
  8. Shanthi, G.; Subbulakshmi, G.; Perumal, P. T. Tetrahedron 2007, 63, 2057. https://doi.org/10.1016/j.tet.2006.12.042
  9. Dabiri, M.; Bahramnejad, M.; Baghbanzadeh, M. Tetrahedron 2009, 65, 9443. https://doi.org/10.1016/j.tet.2009.08.070
  10. Zhu, S. L.; Ji, S. J.; Zhang, Y. Tetrahedron 2007, 63, 9365. https://doi.org/10.1016/j.tet.2007.06.113
  11. Yuling, L.; Hui, C.; Chunling, S.; Daqing, S.; Shunjun, J. J. Comb. Chem. 2010, 12, 231. https://doi.org/10.1021/cc9001185
  12. Kolla, S. R.; Lee, Y. R. Tetrahedron 2012, 68, 226. https://doi.org/10.1016/j.tet.2011.10.060
  13. Bachman, M.; Mann, S. E.; Sheppard, T. D. Org. Biomol. Chem. 2012, 10, 162. https://doi.org/10.1039/c1ob06534c
  14. Ramon, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602. https://doi.org/10.1002/anie.200460548
  15. Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2007, 72, 1263. https://doi.org/10.1021/jo062140i
  16. Jafari, A. A.; Moradgholi. Synth. Commun. 2011, 41, 594. https://doi.org/10.1080/00397911003629473
  17. Khatik, G. L.; Kumar, R.; Chakraborti, A. K. Synthesis 2007, 4, 541.
  18. Kamble, V. T.; Ekhe, V. R.; Joshi, N. S.; Biradar, A. V. Synlett 2007, 9, 1379.
  19. Alinezhad, H.; Tajbakhsh, M.; Tehrani, S. S. Bull. Korean Chem. Soc. 2011, 32, 1543. https://doi.org/10.5012/bkcs.2011.32.5.1543
  20. Hari, G. S.; Lee, Y. R. Synthesis 2010, 3, 453.

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