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Ecofriendly and efficient multicomponent method for preparation of 1-amidoalkyl-2-naphthols using maltose under solvent-free conditions

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Abstract

An efficient and entirely green protocol for preparation of 1-amidoalkyl-2-naphthols employing a multicomponent one-pot condensation reaction of 2-naphthol, amides or urea, and aromatic aldehydes in the presence of maltose under solvent-free conditions is described. The present approach of this methodology offers several advantages such as mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign and simple work-up procedures.

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References

  1. L.W. Xu, C.G. Xia, L. Li, J. Org. Chem. 69, 8482 (2004)

    Article  CAS  Google Scholar 

  2. A. Dömling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  3. S. Knapp, Chem. Rev. 95, 1859 (1995)

    Article  CAS  Google Scholar 

  4. A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999)

    Article  CAS  Google Scholar 

  5. S. Damavandi, R. Sandaroos, Res. Chem. Intermed. doi:10.1007/s11164-012-0681-z

  6. I. Szatmari, F. Fulop, Curr. Org. Synth. 1, 155 (2004)

    Article  CAS  Google Scholar 

  7. J.W. Engels, J. Parsch, J. Parsch, in Molecular Biology in Medicinal Chemistry, ed. by T. Dingermann, D. Steinhilber, G. Folkers (Wiley, Chichester, 2004)

    Google Scholar 

  8. M. Damodiran, N. Panneer, P.T. Perumal, Tetrahedron Lett. 50, 5474 (2009)

    Article  CAS  Google Scholar 

  9. Y.F. Wang, T. Izawa, S. Kobayashi, M. Ohono, J. Am. Chem. Soc. 104, 6465 (1982)

    Article  CAS  Google Scholar 

  10. M.C. Wani, H.L. Taylor, M.E. Wall, J. Chem. Soc. Chem. Commun. 5, 390 (1973)

    Article  Google Scholar 

  11. H.S. Mosher, M.B. Frankel, M. Gregory, J. Am. Chem. Soc. 75, 5326 (1953)

    Article  CAS  Google Scholar 

  12. J.L. Peglion, J. Vian, N. Despaux, V. Audinot, M. Millan, Bioorg. Med. Chem. Lett. 7, 881 (1997)

    Article  CAS  Google Scholar 

  13. 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)

    Article  CAS  Google Scholar 

  14. F. Benedini, G. Bertolini, R. Cereda, G. Dona, G. Gromo, S. Levi, J. Mizrahi, A. Sala, J. Med. Chem. 38, 130 (1995)

    Article  CAS  Google Scholar 

  15. 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)

    Article  CAS  Google Scholar 

  16. 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)

    Article  CAS  Google Scholar 

  17. S. Kantevari, S.V.N. Vuppalapati, L. Nagarapu, Catal. Commun. 8, 1857 (2007)

    Article  CAS  Google Scholar 

  18. N.P. Selvam, P.T. Perumal, Tetrahedron Lett. 47, 7481 (2006)

    Article  CAS  Google Scholar 

  19. B. Das, K.B. Ravikanth, B.R. Rao, J. Mol. Catal. A 261, 180 (2007)

    Article  CAS  Google Scholar 

  20. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Aboonajmi, M. Safarzaei, Chem. Sci. Trans. 8, 426 (2013)

    Google Scholar 

  21. S.A.R. Mulla, T.A. Salama, M.Y. Pathan, S.M. Inamdar, S.S. Chavan, Tetrahedron Lett. 54, 672 (2013)

    Article  CAS  Google Scholar 

  22. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron 69, 212 (2013)

    Article  CAS  Google Scholar 

  23. L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, Iran. J. Catal. 1, 1 (2011)

    CAS  Google Scholar 

  24. M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, N. Hazeri, A. Davodi, S.S. Sajadikhah, Tetrahedron 67, 8492 (2011)

    Article  CAS  Google Scholar 

  25. R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 901 (2013)

    Article  CAS  Google Scholar 

  26. M.R. Mousavi, N. Hazeri, M.T. Maghsoodlou, S. Salahi, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 411 (2013)

    Article  CAS  Google Scholar 

  27. M.M. Khodaei, A.R. Khosropour, H. Moghanian, Synlett 6, 916 (2006)

    Article  Google Scholar 

  28. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, A. Parhami, A. Khalafi-Nezhad, Appl. Catal. A 386, 179 (2010)

    Article  CAS  Google Scholar 

  29. S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Ultrason. Sonochem. 14, 515 (2007)

    Article  CAS  Google Scholar 

  30. M. Wang, Y. Liang, Monatsh. Chem. 142, 153 (2011)

    Article  CAS  Google Scholar 

  31. A.R. Hajipour, Y. Ghayeb, N. Sheikhan, A.E. Ruoho, Tetrahedron Lett. 50, 5649 (2009)

    Article  CAS  Google Scholar 

  32. S.A.M.K. Ansari, J.N. Sangshetti, N.D. Kokare et al., Indian J. Chem. Technol. 17, 71 (2010)

    CAS  Google Scholar 

  33. G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron Lett. 50, 7220 (2009)

    Article  CAS  Google Scholar 

  34. S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Synth. Commun. 37, 1659 (2007)

    Article  CAS  Google Scholar 

  35. G.H. Mahdavinia, M.A. Bigdeli, M.M. Heravi, Chin. Chem. Lett. 19, 1171 (2008)

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan.

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Correspondence to Nourallah Hazeri.

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Adrom, B., Hazeri, N., Maghsoodlou, M.T. et al. Ecofriendly and efficient multicomponent method for preparation of 1-amidoalkyl-2-naphthols using maltose under solvent-free conditions. Res Chem Intermed 41, 4741–4747 (2015). https://doi.org/10.1007/s11164-014-1564-2

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  • DOI: https://doi.org/10.1007/s11164-014-1564-2

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