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Carbon-based Solid Acid Catalyzed One-pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds

  • Received : 2010.11.09
  • Accepted : 2010.12.14
  • Published : 2011.02.20

Abstract

A simple and efficient method for the synthesis of $\beta$-amino carbonyl compounds by one-pot three-component Mannich reaction of acetophenone, aromatic aldehydes and aromatic amines using a carbon-based solid acid (CBSA), as an effective and reusable catalyst, is described. The present methodology offers several advantages such as simple procedure with an easy work-up, shorter reaction times, and high yields.

Keywords

References

  1. Thomson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. https://doi.org/10.1021/cr9402081
  2. Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3169.
  3. Dandia, A.; Singh, R.; Sarawgi, P.; Khaturia, S. Chin. J. Chem. 2006, 24, 950. https://doi.org/10.1002/cjoc.200690180
  4. Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044. https://doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E
  5. Mogilaiah, k.; Kankaiah, G. Indian J. Heterocycl. Chem. 2002, 11, 283.
  6. Kidwai, M.; Bhatnagar, D.; Mishra, N. K.; Bansal, V. Catal. Commun. 2008, 9, 2547. https://doi.org/10.1016/j.catcom.2008.07.010
  7. Akiyama, T.; Matsuda, K.; Fuchibe, K. Synlett 2005, 2, 322.
  8. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 7, 1045.
  9. Akiyama, T.; Itoh, J.; Fuchibe, K. Synlett 2002, 8, 1269.
  10. Wang, L.; Han, J.; Sheng, J.; Tian, H.; Fan, Z. Catal. Commun. 2005, 6, 201. https://doi.org/10.1016/j.catcom.2004.12.009
  11. Li, Z.; Ma, X.; Liu, J.; Feng, X.; Tian, G.; Zhu, A. J. Mol. Catal. A: Chem. 2007, 272, 132. https://doi.org/10.1016/j.molcata.2007.03.029
  12. Li, H.; Zeng, H.; Shao, H. Tetrahedron Lett. 2009, 50, 6858. https://doi.org/10.1016/j.tetlet.2009.09.131
  13. Zeng, H.; Li, H.; Shao, H. Ultrason. Sonochem. 2009, 16, 758. https://doi.org/10.1016/j.ultsonch.2009.03.008
  14. Ollevier, T.; Nadeau, E. Synlett 2006, 2, 219.
  15. Okuhara, T. Chem. Rev. 2002, 102, 3641. https://doi.org/10.1021/cr0103569
  16. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayashi, S.; Domen, K. Angew. Chem., Int. Ed. 2004, 43, 2955. https://doi.org/10.1002/anie.200453947
  17. Zhou, L.; Liu, K.; Hua, W. M.; Yue, Y. H.; Gao, Z. Chin. J. Chem. 2009, 30, 196.
  18. Davoodnia, A.; Bakavoli, M.; Barakouhi, Gh.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2007, 18, 1483. https://doi.org/10.1016/j.cclet.2007.10.013
  19. Davoodnia, A.; Roshani, M.; Malaeke, S. H.; Bakavoli, M. Chin. Chem. Lett. 2008, 19, 525. https://doi.org/10.1016/j.cclet.2008.01.037
  20. Davoodnia, A.; Heravi, M. M.; Rezaei-Daghigh, L.; Tavakoli-Hoseini, N. Monatsh. Chem. 2009, 140, 1499. https://doi.org/10.1007/s00706-009-0193-8
  21. Davoodnia, A.; Bakavoli, M.; Moloudi, R.; Khashi, M.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2010, 21, 1. https://doi.org/10.1016/j.cclet.2009.09.002
  22. Davoodnia, A.; Bakavoli, M.; Moloudi, R.; Khashi, M.; Tavakoli-Hoseini, N. Monatsh. Chem. 2010, 141, 867. https://doi.org/10.1007/s00706-010-0329-x
  23. Davoodnia, A.; Heravi, M. M.; Safavi-Rad, Z.; Tavakoli-Hoseini, N. Synth. Commun. 2010, 40, 2588. https://doi.org/10.1080/00397910903289271
  24. Davoodnia, A.; Heravi, M. M.; Rezaei-Daghigh, L.; Tavakoli-Hoseini, N. Chin. J. Chem. 2010, 28, 429. https://doi.org/10.1002/cjoc.201090091
  25. Davoodnia, A.; Allameh, S.; Fakhari, A. R.; Tavakoli-Hoseini, N. Chin. Chem. Lett. 2010, 21, 550. https://doi.org/10.1016/j.cclet.2010.01.032
  26. Tavakoli-Hoseini, N.; Davoodnia, A. Asian J. Chem. 2010, 22, 7197.
  27. Davoodnia, A. Asian J. Chem. 2010, 22, 1595.

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