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CeCl3·7H2O-NaI-SiO2 Catalyzed Aza-Michael Addition of N-Heterocycles to Enones under Solvent Free Conditions

  • Received : 2012.08.01
  • Accepted : 2012.08.16
  • Published : 2012.11.20
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Abstract

Keywords

References

  1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: New York, 1992; p 114.
  2. Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991. https://doi.org/10.1016/S0040-4020(02)00991-2
  3. Xu, L.-W.; Xia, C.-G. Eur. J. Org. Chem. 2005, 633.
  4. Krishna, P. R.; Sreeshailam, A.; Srinivas, R. Tetrahedron 2009, 65, 9657. https://doi.org/10.1016/j.tet.2009.08.021
  5. Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 23, 827. https://doi.org/10.1246/cl.1994.827
  6. Loh, T.-P.; Wei, L.-L. Synlett 1998, 975.
  7. Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891. https://doi.org/10.1016/S0040-4039(02)00654-8
  8. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 720.
  9. Xu, L.-W.; Li, L.; Xia, C.-G. Hel. Chim. Acta 2004, 87, 1522. https://doi.org/10.1002/hlca.200490139
  10. Reboule, I.; Gil, R.; Collin, J. Tetrahedron Lett. 2005, 46, 7761. https://doi.org/10.1016/j.tetlet.2005.09.039
  11. Duan, Z.; Xuan, X.; Li, T.; Yang, C.; Wu, Y. Tetrahedron Lett. 2006, 5433.
  12. Azizi, N.; Baghi, R.; Ghafuri, H.; Bolourtchian, M.; Mohammad, H. Synlett 2010, 379.
  13. Reimlinger, H.; Oth, J. F. M. Chem. Ber. 1964, 97, 331. https://doi.org/10.1002/cber.19640970205
  14. Ferroni, R.; Milani, L.; Simoni, D.; Orlandini, P.; Guarneri, M.; Franze, D.; Bardi, A. IL Farmaco. 1989, 44, 495.
  15. Weintraub, P. M.; Tiernan, P. L.; Huffman, J. C. J. Heterocycl. Chem. 1987, 24, 561. https://doi.org/10.1002/jhet.5570240305
  16. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109. https://doi.org/10.1021/jo026550s
  17. Bartoli, G.; Bartolacci, M.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Torregiani, E. J. Org. Chem. 2005, 70, 169. https://doi.org/10.1021/jo048329g
  18. Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Adv. Synth. Catal. 2005, 347, 655. https://doi.org/10.1002/adsc.200404348
  19. Reddy, K. R.; Kumar, N. S. Synlett 2006, 2246.
  20. Aburatani, S.; Kawatsura, M.; Uenishi, J. Heterocycles 2007, 71, 189. https://doi.org/10.3987/COM-06-10935
  21. Liu, B. K.; Wu, Q.; Qian, X. Q.; Lv, D. S.; Lin, X. F. Synthesis 2007, 17, 2653.
  22. Uddin, M. I.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2008, 1402.
  23. Zhou, Y.; Li, X.; Li, W.; Wu, C.; Liang, X.; Ye, J. Synlett 2010, 2357.
  24. Xu, W. F.; Chen, Q.; Liu, R. Q.; Ren, F. B.; Zhou, Y. F.; Lu, X. L. Asian J. Chem. 2011, 23, 4165.
  25. Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052. https://doi.org/10.1021/jo0108764
  26. Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantori, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 4594.
  27. Choi, I. Y.; Lim, H. J.; Lee, G. C.; Park, U. G.; Kong, J. Y. KR20090090457 A.
  28. Lee, I. Y. C.; Yu, O. J.; Lim, H.-J.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 723. https://doi.org/10.5012/bkcs.2008.29.4.723
  29. Garcia, M. A.; Lopez, C.; Claramunt, R. M.; Kenz, A.; Pierrot, M.; Elguero, J. Hel. Chim. Acta 2002, 85, 2763. https://doi.org/10.1002/1522-2675(200209)85:9<2763::AID-HLCA2763>3.0.CO;2-R
  30. Bellina, F.; Cauteruccio, S.; Rossi, R. J. Org. Chem. 2007, 72, 8543. https://doi.org/10.1021/jo701496p
  31. Xu, L.; Zhang, S.; Trudell, M. L. Chem. Commun. 2004, 1668.
  32. Atkinson, M. R.; Polya, J. B. J. Chem. Soc. 1954, 3319. https://doi.org/10.1039/jr9540003319
  33. Jin, T.; Kamijo, S.; Yamamoto, Y. Eur. J. Org. Chem. 2004, 3789.

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