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Journal of Chemistry
Volume 2013, Article ID 341649, 5 pages
http://dx.doi.org/10.1155/2013/341649
Research Article

Efficient Synthesis of 1-Amidoalkyl-2-Naphthols by One-Pot, Three-Component Reaction under Solvent-Free Conditions

Department of Chemistry, Firoozabad Branch, Islamic Azad University, P.O. Box 74715-117, Firoozabad, Fars, Iran

Received 7 June 2012; Revised 12 July 2012; Accepted 27 July 2012

Academic Editor: Andrea Trabocchi

Copyright © 2013 Zahed Karimi-Jaberi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. Shaabani, A. Maleki, A. H. Rezayan, and A. Sarvary, “Recent progress of isocyanide-based multicomponent reactions in Iran,” Molecular Diversity, vol. 15, no. 1, pp. 41–68, 2011. View at Publisher · View at Google Scholar · View at Scopus
  2. M. J. Climent, A. Corma, and S. Iborra, “Homogeneous and heterogeneous catalysts for multicomponent reactions,” RSC Advances, vol. 2, no. 1, pp. 16–58, 2012. View at Publisher · View at Google Scholar · View at Scopus
  3. D. Seebach and J. L. Matthews, “β-peptides: a surprise at every turn,” Chemical Communications, no. 21, pp. 2015–2022, 1997. View at Google Scholar · View at Scopus
  4. Y. F. Wang, T. Izawa, S. Kobayashi, and M. Ohno, “Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction,” Journal of the American Chemical Society, vol. 104, no. 23, pp. 6465–6466, 1982. View at Google Scholar · View at Scopus
  5. S. Knapp, “Synthesis of complex nucleoside antibiotics,” Chemical Reviews, vol. 95, no. 6, pp. 1859–1876, 1995. View at Google Scholar · View at Scopus
  6. E. Juaristi, Enantioselective Synthesis of β-Amino Acids, John Wiley & Sons, New York, NY, USA, 1997.
  7. A. Y. Shen, C. T. Tsai, and C. L. Chen, “Synthesis and cardiovascular evaluation of N-substituted 1- aminomethyl-2-naphthols,” European Journal of Medicinal Chemistry, vol. 34, no. 10, pp. 877–882, 1999. View at Publisher · View at Google Scholar · View at Scopus
  8. S. Kantevari, S. V. N. Vuppalapati, and L. Nagarapu, “Montmorillonite K10 catalyzed efficient synthesis of amidoalkyl naphthols under solvent free conditions,” Catalysis Communications, vol. 8, no. 11, pp. 1857–1862, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. N. P. Selvam and P. T. Perumal, “A new synthesis of acetamido phenols promoted by Ce(SO4)2,” Tetrahedron Letters, vol. 47, no. 42, pp. 7481–7483, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. B. Das, K. Laxminarayana, B. Ravikanth, and B. R. Rao, “Iodine catalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions,” Journal of Molecular Catalysis A, vol. 261, no. 2, pp. 180–183, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. L. Nagarapu, M. Baseeruddin, S. Apuri, and S. Kantevari, “Potassium dodecatungstocobaltate trihydrate (K5CoW12O40· 3H2O): a mild and efficient reusable catalyst for the synthesis of amidoalkyl naphthols in solution and under solvent-free conditions,” Catalysis Communications, vol. 8, no. 11, pp. 1729–1734, 2007. View at Publisher · View at Google Scholar · View at Scopus
  12. H. R. Shaterian, H. Yarahmadi, and M. Ghashang, “An efficient, simple and expedition synthesis of 1-amidoalkyl-2-naphthols as “drug like” molecules for biological screening,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 2, pp. 788–792, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. G. H. Mahdavinia, M. A. Bigdeli, and M. M. Heravi, “Silica supported perchloric acid (HClO4-SiO2): a mild, reusable and highly efficient heterogeneous catalyst for the synthesis of amidoalkyl naphthols,” Chinese Chemical Letters, vol. 19, no. 10, pp. 1171–1174, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. G. C. Nandi, S. Samai, R. Kumar, and M. S. Singh, “Atom-efficient and environment-friendly multicomponent synthesis of amidoalkyl naphthols catalyzed by P2O5,” Tetrahedron Letters, vol. 50, no. 51, pp. 7220–7222, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. A. R. Hajipour, Y. Ghayeb, N. Sheikhan, and A. E. Ruoho, “Brønsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solvent-free conditions,” Tetrahedron Letters, vol. 50, no. 40, pp. 5649–5651, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. M. M. Heravi, N. Tavakoli-Hoseini, and F. F. Bamoharram, “Brønsted acidic ionic liquids as efficient catalysts for the synthesis of amidoalkyl naphthols,” Synthetic Communications, vol. 41, no. 2, pp. 298–306, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. S. A. M. K. Ansari, J. N. Sangshetti, N. D. Kokare, P. S. Wakte, and D. B. Shinde, “Oxalic acid catalyzed solvent-free synthesis of α-amidoalkyl-β- naphthols,” Indian Journal of Chemical Technology, vol. 17, no. 1, pp. 71–73, 2010. View at Google Scholar · View at Scopus
  18. J. Luo and Q. Zhang, “A one-pot multicomponent reaction for synthesis of 1-amidoalkyl-2-naphthols catalyzed by PEG-based dicationic acidic ionic liquids under solvent-free conditions,” Monatshefte fur Chemie, vol. 142, pp. 923–930, 2011. View at Publisher · View at Google Scholar · View at Scopus
  19. Q. Zhang, J. Luo, and Y. Wei, “A silica gel supported dual acidic ionic liquid: an efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols,” Green Chemistry, vol. 12, no. 12, pp. 2246–2254, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. D. A. Kotadia and S. S. Soni, “Silica gel supported −SO3H functionalised benzimidazolium based ionic liquid as a mild and effective catalyst for rapid synthesis of 1-amidoalkyl naphthols,” Journal of Molecular Catalysis A, vol. 353-354, pp. 44–49, 2012. View at Publisher · View at Google Scholar · View at Scopus
  21. Z. Karimi-Jaberi and M. M. ReyazoShams, “Trichloroacetic acid as a solid heterogeneous catalyst for the rapid synthesis of dihydropyrano[2,3-c]pyrazoles under solvent-free conditions,” Heterocyclic Communications, vol. 17, no. 5-6, pp. 177–179, 2011. View at Publisher · View at Google Scholar · View at Scopus
  22. Z. Karimi-Jaberi, S. Z. Abbasi, B. Pooladian, and M. Jokar, “Efficient, one-pot synthesis of tetrahydrobenzo[a]xanthen-11-ones and dibenzo[a,j]xanthenes using trichloroacetic acid as a solid heterogeneous catalyst under solvent-free conditions,” E-Journal of Chemistry, vol. 8, no. 4, pp. 1895–1899, 2011. View at Google Scholar · View at Scopus
  23. Z. Karimi-Jaberi and B. Pooladian, “A facile synthesis of new 2-amino-4 h -pyran-3-carbonitriles by a one-pot reaction of α, α′-Bis(arylidene) cycloalkanones and malononitrile in the presence of K2CO3,” The Scientific World Journal, vol. 2012, Article ID 208796, 5 pages, 2012. View at Publisher · View at Google Scholar · View at Scopus
  24. Z. Karimi-Jaberi and B. Pooladian, “A facile synthesis of α,α′-bis(substituted benzylidene) cycloalkanones catalyzed by p-TSA under solvent-free conditions,” Green Chemistry Letters and Reviews, vol. 5, no. 2, pp. 187–193, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. E. V. Anslyn and D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, Calif, USA, 2006.