Citation: Arash Ghorbani-Choghamarani, Shima Rashidimoghadam. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1024-1029. doi: 10.1016/S1872-2067(14)60029-2 shu

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions

1.
Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran

Corresponding author: Arash Ghorbani-Choghamarani,
Received Date: 17 December 2013
Available Online: 9 January 2014
Fund Project:

A facile and efficient method has been developed for the synthesis of 1-amidoalkyl-2-naphthols via the one-pot multi-component condensation of 2-naphthol with aromatic aldehydes and acetamide or thioacetamide in the presence of melamine-Br₃ under solvent-free conditions. There are several advantages to this reaction, including high yields, short reaction time, and high catalytic efficiency.
- Multi-component reaction,
- Amidoalkyl naphthol,
- Tribromo-melamine,
- Solvent-free,
- One-pot
1. [1]
  [1] Wang Y F, Izawa T, Kobayashi S, Ohno M. J Am Chem Soc, 1982, 104: 6465
2. [2]
  [2] Knapp S. Chem Rev, 1995, 95: 1859
3. [3]
  [3] Shen A Y, Chen C L, Lin C I. Chin J Physiol, 1992, 35: 45
4. [4]
  [4] Szatmári I, Fülöp F. Curr Org Synth, 2004, 1: 155
5. [5]
  [5] Shen A Y, Tsai C T, Chen C L. Eur J Med Chem, 1999, 34: 877
6. [6]
  [6] Zhu X Y, Lee Y R, Kim S H. Bull Korean Chem Soc, 2012, 33: 2799
7. [7]
  [7] Nagawade R R, Shinde D B. Chin J Chem, 2007, 25: 1710
8. [8]
  [8] Patil S B, Singh P R, Surpur M P, Samant S D. Ultrason Sonochem, 2007, 14: 515
9. [9]
  [9] Selvam N P, Perumal P T. Tetrahedron Lett, 2006, 47: 7481
10. [10]
  [10] Rashinkar G, Salunkhe R. J Mol Catal A, 2010, 316: 146
11. [11]
  [11] Wang M, Liang Y, Zhang T T, Gao J J. Chin Chem Lett, 2012, 23: 65
12. [12]
  [12] Nagarapu L, Baseeruddin M, Apuri S, Kantevari S. Catal Commun, 2007, 8: 1729
13. [13]
  [13] Hong M, Cai C, Yi W B. Chin Chem Lett, 2011, 22: 322
14. [14]
  [14] Dorehgiraee A, Khabazzadeh H, Saidi K. Arkivoc, 2009, (7): 303
15. [15]
  [15] Kumar A, Rao M S, Ahmad I, Khungar B. Can J Chem, 2009, 87: 714
16. [16]
  [16] Shaterian H R, Yarahmadi H, Ghashang M. Bioorg Med Chem Lett, 2008, 18: 788
17. [17]
  [17] Kantevari S, Vuppalapati S V N, Nagarapu L. Catal Commun, 2007, 8: 1857
18. [18]
  [18] Khodaei M M, Khosropour A R, Moghanian H. Synlett, 2006: 916
19. [19]
  [19] Supale A R, Gokavi G S. J Chem Sci, 2010, 122: 189
20. [20]
  [20] Mistry S R, Joshi R S, Maheria K C. J Chem Sci, 2011, 123: 427
21. [21]
  [21] Zhang P, Zhang Z H. Monatsh Chem, 2009, 140: 199
22. [22]
  [22] Das B, Laxminarayana K, Ravikanth B, Rao B R. J Mol Catal A, 2007, 261: 180
23. [23]
  [23] Khaksar S, Najafi R, Ostad S M, Tajbakhsh M. World Appl Sci J, 2012, 20: 656
24. [24]
  [24] Kiasat A R, Mouradzadegun A, Saghanezhad S J. Chin J Catal (催化学报), 2013, 34: 1861
25. [25]
  [25] Wu L Q. Eur J Chem, 2012, 9: 1035
26. [26]
  [26] Ghorbani-Choghamarani A, Zolfigol M A, Hajjami M, Jafari S. J Chin Chem Soc, 2008, 55: 1208
27. [27]
  [27] Zare A, Hasaninejad A, Rostami E, Moosavi-Zare A R, Pishahang N, Roshankar M, Khedri F, Khedri M. Eur J Chem, 2010, 7: 1162
28. [28]
  [28] Zolfigol M A, Ghorbani-Vaghei R, Mallakpour S, Chehardoli G, Ghorbani-Choghamarani A, Yazdi A H. Synthesis, 2006: 1631
29. [29]
  [29] Ghorbani-Choghamarani A, Amani K, Zolfigol M A, Hajjami M, Ayazi-Nasrabadi R. J Chin Chem Soc, 2009, 56: 255
30. [30]
  [30] Liu Y L, Shi T D, Zhou F, Zhao X L, Wang X, Zhou J. Org Lett, 2011, 13: 3826
31. [31]
  [31] Liu Y L, Zeng X P, Zhou J. Chem Asian J, 2012, 7: 1759
32. [32]
  [32] Liu Y L, Zhou J. Chem Commun, 2013, 49: 4421
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br3 under solvent-free conditions

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通讯作者: 陈斌, bchen63@163.com

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions