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Preparation of amidoalkyl naphthols by a three-component reaction catalyzed by 2,4,6-trichloro-1,3,5-triazine under solvent-free conditions

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Abstract

An efficient one-pot synthesis of amidoalkyl naphthols is described. This involves the three-component reaction of 2-naphthol, aromatic aldehydes and amide or urea in the presence of a catalytic amount of 2,4,6-trichloro-1,3,5-triazine (TCT, cyanuric chloride) under solvent-free conditions.

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References

  1. Dömling A (2006) Chem Rev 106:17

    Article  CAS  Google Scholar 

  2. Shestopalov AM, Shestopalov AA, Rodinovskaya LA (2008) Synthesis:1

  3. Mironov MA (2006) QSAR Comb Sci 25:423

    Article  CAS  Google Scholar 

  4. Knapp S (1995) Chem Rev 95:1859

    Article  CAS  Google Scholar 

  5. Szatmári I, Fülöp F (2004) Curr Org Synth 1:155

    Article  Google Scholar 

  6. Shen AY, Tsai CT, Chen CL (1999) Eur J Med Chem 34:877

    Article  CAS  Google Scholar 

  7. Anary-Abbasinejad M, Hassanabadi A, Kamali-Gharamaleki M, Saidipoor A, Anaraki-Ardakani H (2007) J Chem Res: 644

  8. Khodaei MM, Khosropour AR, Moghanian H (2006) Synlett: 916

  9. Shaterian HR, Yarahmadi H (2008) Arkivoc ii:105

    Google Scholar 

  10. Shaterian HR, Yarahmadi H, Ghashang M (2008) Bioorg Med Chem Lett 18:788

    Article  CAS  Google Scholar 

  11. Su WK, Tang WY, Li JJ (2008) J Chem Res: 123

  12. Das B, Laxminarayana K, Ravikanth B, Rao R (2007) J Mol Catal A Chem 261:180

    Article  CAS  Google Scholar 

  13. Nagarapu L, Baseeruddin M, Apuri S, Kantevari S (2007) Catal Commun 8:1729

    Article  CAS  Google Scholar 

  14. Patil SB, Singh PR, Surpur MP, Samant SD (2007) Synth Commun 37:1659

    Article  CAS  Google Scholar 

  15. Shaterian HR, Yarahmadi H, Ghashang M (2008) Tetrahedron 64:1263

    Article  CAS  Google Scholar 

  16. Das B, Kumar DN, Laxminarayana K, Ravikanth B (2007) Helv Chim Acta 90:1330

    Article  CAS  Google Scholar 

  17. Shaterian HR, Yarahmadi H (2008) Tetrahedron Lett 49:1297

    Article  CAS  Google Scholar 

  18. Kantevari S, Vuppalapati SVN, Nagarapu L (2007) Catal Commun 8:1857

    Article  CAS  Google Scholar 

  19. Srihari G, Nagaraju M, Murthy MM (2007) Helv Chim Acta 90:1497

    Article  CAS  Google Scholar 

  20. Patil SB, Singh PR, Surpur MP, Samant SD (2007) Ultrason Sonochem 14:515

    Article  CAS  Google Scholar 

  21. Nagawade RR, Shinde DB (2007) Chin J Chem 25:1710

    Article  CAS  Google Scholar 

  22. Blotny G (2006) Tetrahedron 62:9507

    Article  CAS  Google Scholar 

  23. Haval KP (2006) Synlett: 2156

  24. Bandgar BP, Joshi NS, Kamble VT, Sawant SS (2008) Aust J Chem 61:231

    Article  CAS  Google Scholar 

  25. Khalafi-Nezhad A, Zare A, Parhami A, Rad MNS, Nejabat GR (2007) Phosphorus Sulfur Silicon Relat Elem 182:657

    Article  CAS  Google Scholar 

  26. Bandgar BP, Joshi NS, Bettigeri SV (2007) Monatsh Chem 138:67

    Article  CAS  Google Scholar 

  27. Gao S, Tu Z, Kuo C-W, Liu J-T, Chu C-M, Yao C-F (2006) Org Biomol Chem 4:2851

    Article  CAS  Google Scholar 

  28. Das B, Laxminarayana K, Ravikanth B (2006) Tetrahedron Lett 47:9103

    Article  CAS  Google Scholar 

  29. Bandgar BP, Joshi NS, Kamble VT (2006) Tetrahedron Lett 47:4775

    Article  CAS  Google Scholar 

  30. Sharma GVM, Reddy KL, Lakshmi PS, Krishna PR (2006) Synthesis: 55

  31. Das B, Kumar RA, Thirupathi P (2007) Helv Chim Acta 90:1206

    Article  CAS  Google Scholar 

  32. Roy S, Das T, Saha M, Chaudhuri SK, Bhar S (2007) Synth Commun 37:4367

    Article  CAS  Google Scholar 

  33. Bigdeli MA, Mahdavinia GH, Jafari S, Hazarkhani H (2007) Catal Commun 8:2229

    Article  CAS  Google Scholar 

  34. Bigdeli MA, Heravi MM, Mahdavinia GH (2007) Catal Commun 8:1595

    Article  CAS  Google Scholar 

  35. Zhang Z-H, Tao X-Y (2008) Aust J Chem 61:77

    Article  CAS  Google Scholar 

  36. Zhang Z-H (2005) Monatsh Chem 136:1191

    Article  CAS  Google Scholar 

  37. Zhang Z-H, Li T-S, Li J-J (2007) Monatsh Chem 138:89

    Article  CAS  Google Scholar 

  38. Mo L-P, Ma Z-C, Zhang Z-H (2005) Synth Commun 35:1997

    Article  CAS  Google Scholar 

  39. Zhang Z-H, Li J-J, Gao Y-Z, Liu Y-H (2007) J Heterocyclic Chem 44:1509

    Article  CAS  Google Scholar 

  40. Zhang Z-H, Yang S-T, Lin J (2006) Synth Commun 36:1645

    Article  CAS  Google Scholar 

  41. Zhang Z-H, Lin J (2007) Synth Commun 37:209

    Article  CAS  Google Scholar 

  42. Zhang Z-H, Hu J-Y (2006) J Braz Chem Soc 17:1447

    CAS  Google Scholar 

  43. Cui Z-S, Zhang Z-H, Liu S-F (2006) J Chem Res: 390

  44. Li J-J, Tao X-Y, Zhang Z-H (2008) Phosphorus Sulfur Silicon Relat Elem 183:1672

    Article  CAS  Google Scholar 

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Acknowledgments

We thank the Science Foundation from Hebei Normal University (L20061314), the Nature Science Foundation of Hebei Province (B2008000149) and the Natural Science Foundation of Hebei Education Department (2006318) for financial support.

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Correspondence to Zhan-Hui Zhang.

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Zhang, P., Zhang, ZH. Preparation of amidoalkyl naphthols by a three-component reaction catalyzed by 2,4,6-trichloro-1,3,5-triazine under solvent-free conditions. Monatsh Chem 140, 199–203 (2009). https://doi.org/10.1007/s00706-008-0059-5

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  • DOI: https://doi.org/10.1007/s00706-008-0059-5

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