Zirconyl triflate as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions
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  • 作者:Hajar Hashemi (1)
    Ali Reza Sardarian (1)
  • 关键词:β ; Naphthol ; Zirconyl triflate ; Solvent ; free ; 1 ; Amidoalkyl ; 2 ; naphthol
  • 刊名:Journal of the Iranian Chemical Society
  • 出版年:2013
  • 出版时间:August 2013
  • 年:2013
  • 卷:10
  • 期:4
  • 页码:745-750
  • 全文大小:1114KB
  • 参考文献:1. Y. Rubin, S. Lin, C.B. Knobler, J. Antthjony, A.M. Boldi, F. Diederich, J. Am. Chem. Soc. 113, 6943 (1991) CrossRef
    2. A. Chetia, C.J. Saikia, K.C. Lekhok, R.C. Boruah, Tetrahedron. Lett. 45, 2649 (2004) CrossRef
    3. H.R. Shaterian, H. Yarahmadi, M. Ghashang, Tetrahedron 64, 1263 (2008) CrossRef
    4. A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty, M.S. Manhas, Tetrahedron. Lett. 45, 8351 (2004) CrossRef
    5. G.F. Ross, E. Herdtweck, I. Ugi, Tetrahedron 58, 6127 (2002) CrossRef
    6. T. Akiyama, K. Matsuda, K. Fuchibe, Synlett 322 (2005)
    7. T. Dingermann, D. Steinhilber, G. Folkers, / Molecular biology in medicinal chemistry (Wiley-VCH, Weinheim, 2004)
    8. A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999) CrossRef
    9. A.Y. Shen, C.L. Chen, C.I. Lin, Chin. J. Physiol. 35, 45 (1992)
    10. M. Damodiran, N.P. Selvam, P.T. Perumal, Tetrahedron. Lett. 50, 5474 (2009) CrossRef
    11. T. Haneishi, T. Okazaki, T. Hata, C. Tamura, M. Nomura, A. Naito, I. Seki, M. Arai, J. Antibiot. 24; 797 (1971)
    12. K. Sasaki, Y. Kusakabe, S. Esumi, J. Antibiot. 25, 151 (1972) CrossRef
    13. Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, S. Shirato, J. Antibiot. 25, 44 (1972) CrossRef
    14. M. C. Wani, H. L. Taylor, M.E. Wall, J. Chem. Soc. Chem. Commun. 390 (1973)
    15. P.Y. Johnson, R.B. Silver, J. Heterocycl. Chem. 10, 1029 (1973) CrossRef
    16. S. Remillard, L.I. Rebhun, G.A. Howie, S.M. Kupchan, Science 189, 1002 (1975) CrossRef
    17. T. Urban-ski, D. Ghrne, I. Szczerek, M. Modaski, Polish Patent 54,007 (1967)
    18. G.Y. Lesher, A.R. Surrey, J. Am. Chem. Soc. 77, 636 (1955) CrossRef
    19. H.S. Mosher, M.B. Frankel, M. Gregory, J. Am. Chem. Soc. 75, 5326 (1953) CrossRef
    20. J.L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot, M. Millan, Bioorg. Med. Chem. Lett. 7, 881 (1997) CrossRef
    21. H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna, S. Croft, H. Kendrick, V. Yardley, G. Moyna, Bioorg. Med. Chem. Lett. 11, 1851 (2001) CrossRef
    22. F. Benedini, G. Bertolini, R. Cereda, G. Dona, G. Gromo, S. Levi, J. Mizrahi, A. Sala, J. Med. Chem. 38, 130 (1995) CrossRef
    23. R.D. Clark, J.M. Caroon, A.F. Kluge, D.B. Repke, A.P. Roszkowski, A.M. Strosberg, S. Baker, S.M. Bitter, M.D. Okada, J. Med. Chem. 26, 657 (1983) CrossRef
    24. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, T. Kuroki, J. Med. Chem. 40, 105 (1997) CrossRef
    25. M. Khodaei, A.R. Khosropour, H. Moghanian, Synlett 6, 916 (2006) CrossRef
    26. R.R. Nagawade, D.B. Shinde, Acta. Chim. Slov. 54, 642 (2007)
    27. H.R. Shaterian, H. Yarahmadi, Tetrahedron. Lett. 49, 1297 (2008) CrossRef
    28. S. Kantevari, S.V.N. Vuppalapati, L. Nagarapu, Catal. Commun. 8, 1857 (2007) CrossRef
    29. B. Das, K. Laxminarayana, B. Ravikanth, B.R. Rao, J. Mol. Catal. A Chem. 261, 180 (2007) CrossRef
    30. N.P. Selvam, P.T. Perumal, Tetrahedron. Lett. 47, 7481 (2006) CrossRef
    31. H.R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18, 788 (2008) CrossRef
    32. W. K. Su, W. Y. Tang, J. J. Li,. J. Chem. Res. 123 (2008)
    33. A.R. Hajipour, Y. Ghayeb, N. Sheikhan, A.E. Ruoho, Tetrahedron. Lett. 50, 5649 (2009) CrossRef
    34. M. Lei, L. Ma, L. Hu, Tetrahedron. Lett. 50, 6393 (2009) CrossRef
    35. G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron. Lett. 50, 7220 (2009) CrossRef
    36. A. Kumar, M.S. Rao, I. Ahmad, B. Khungar, Can. J. Chem. 87, 714 (2009) CrossRef
    37. H. Khabazzadeh, K. Saidi, N. Seyedi, J. Chem. Sci. 121, 429 (2009) CrossRef
    38. L.T. An, X.H. Lu, F.Q. Ding, W.Q. Jiang, J.P. Zou, Chin. J. Chem. 26, 2117 (2008) CrossRef
    39. H. R. Shaterian, H. Yarahmadi, ARKIVOC ii 105 (2008)
    40. L. Nagarapu, M. Baseeruddin, S. Apuri, S. Kantevari, Catal. Commun. 8, 1729 (2007) CrossRef
    41. R.R. Nagawade, D.B. Shinde, Chin. J. Chem. 25, 1710 (2007) CrossRef
    42. S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Ultrason. Sonochem. 14, 515 (2007) CrossRef
    43. W.Q. Jiang, L.T. An, J.P. Zou, Chin. J. Chem. 26, 1697 (2008) CrossRef
    44. S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Synth. Commun. 37, 1659 (2007) CrossRef
    45. G. Srihari, M. Nagaraju, M.M. Murthy, Helv. Chim. Acta 90, 1497 (2007) CrossRef
    46. H.R. Shaterian, A. Hosseinian, M. Ghashang, Synth. Comm. 38, 3375 (2008) CrossRef
    47. S.A.M.K. Ansari, J.N. Sangshetti, N.D. Kokare, P.S. Wakte, D.B. Shinde, Indian J. Chem. Tech. 17, 71 (2010)
    48. H.R. Shaterian, A. Hosseinian, M. Ghashang, J. Iran. Chem. Soc. 9, 1 (2012) CrossRef
    49. M. Zandi, A.R. Sardarian, C.R. Chimi. 15, 365 (2012)
    50. H. Firouzabadi, M. Jafarpour, J. Iran. Chem. Soc. 5, 159 (2008) CrossRef
    51. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor- Baltork, S. Chahardahcheric, Z. Tavakoli, J. Organomet. Chem. 693, 2041 (2008) CrossRef
    52. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, M. Babaghanbari, M. Zarea, L. Shariati, S.A. Taghavi, J. Iran. Chem. Soc. 6, 523 (2009) CrossRef
    53. M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, S. Gorjipoor, P. Yazdani, Synth. Commun. 39, 552 (2009) CrossRef
    54. M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, P. Yazdani, S. Ghorjipoor, Heteroatom. Chem. 20, 131 (2009) CrossRef
    55. I. Mohammadpoor-Baltork, M. Moghadam, V. Mirkhani, S. Tangestaninejad, H.R. Tavakoli, Chin. Chem. Lett. 22, 9 (2011) CrossRef
    56. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, L. Shariati, M. Babaghanbari, M. Zarea, J. Iran. Chem. Soc. 6, 789 (2009) CrossRef
  • 作者单位:Hajar Hashemi (1)
    Ali Reza Sardarian (1)

    1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 75454, Iran
  • ISSN:1735-2428
文摘
In the present work, the preparation of 1-amidoalkyl-2-naphthols via one-pot three-component condensation of amides, aldehydes, and β-naphthol in the presence of catalytic amounts of zirconyl triflate, as a highly efficient, low toxic, stable and non-hygroscopic catalyst under solvent-free conditions is reported. This low-cost procedure offers several other advantages such as short reaction times and good to excellent yields.

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