Articles

Copper Benzenesulfonate-Promoted One-Pot Synthesis of 1-Carbamatoalkyl-2-naphthols

  • Wang Min ,
  • Song Jilei ,
  • Wan Xin ,
  • Yang Zhongyong
Expand
  • College of Chemistry, Chemical Engineering and Food Safety, Bohai University, Jinzhou 121013

Received date: 2012-11-06

  Revised date: 2012-12-05

  Online published: 2012-12-20

Abstract

1-Carbamatoalkyl-2-naphthol derivatives were obtained from one-pot three-component condensation of 2-naphthol, aldehydes, and carbamates catalyzed by copper benzenesulfonate under thermal solvent-free conditions. The effects of amount of catalyst, reaction temperature and solvent on the products yields were investigated. Experimental results showed that only 2 mol% copper benzenesulfoante was enough to induce the conversion. After reaction, catalyst could be recycled four times without distinct loss of catalytic activity. The structures of all products were characterized by 1H NMR, 13C NMR, IR, MS techniques and elemental analysis. A mechanism to rationalize the reaction was proposed.

Cite this article

Wang Min , Song Jilei , Wan Xin , Yang Zhongyong . Copper Benzenesulfonate-Promoted One-Pot Synthesis of 1-Carbamatoalkyl-2-naphthols[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 517 -522 . DOI: 10.6023/cjoc201211005

References

[1] Knapp, S. Chem. Rev. 1995, 95, 1859.

[2] Juaristi, E. Enantioselective Synthesis of β-Amino Acids, John Wiley & Sons, New York, 1997, p. 167.

[3] Dingermann, T.; Steinhilber, D.; Folkers, G. Molecular Biology in Medicinal Chemistry, Wiley-VCH, Weinheim, 2004, p. 132.

[4] Shen, A. Y.; Tsai, C. T.; Chen, C. L. Eur. J. Med. Chem. 1999, 34, 877.

[5] Mosslemin, M. H.; Nateghi, M. R.; Mohebat, R. Monatsh. Chem. 2008, 139, 1247.

[6] Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Tetrahedron Lett. 2008, 49, 5804.

[7] Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Synth. Commun. 2009, 39, 2560.

[8] Tavakoli-Hoseini, N.; Heravi, M. M.; Bamoharran, F. F.; Davoodnia, A. Bull. Korean Chem. Soc. 2011, 32, 787.

[9] Reza, S. H.; Asghar, H.; Majid, G. Chin. J. Chem. 2009, 27, 821.

[10] Heravi, M. M.; Tavakoli-Hoseini, N.; Bamoharram, F. F. Green Chem. Lett. Rev. 2010, 3, 263.

[11] Kundu, D.; Majee, A.; Hajra, A. Catal. Commun. 2010, 11, 1157.

[12] Tamaddon, F.; Bistgani, J. M. Synlett 2011, 2947.

[13] Deshmukh, K. M.; Qureshi, Z. S.; Patil, Y. P.; Bhanage, B. M. Synth. Commun. 2012, 42, 93.

[14] Zare, A.; Akbarzadeh, S.; Foroozani, E.; Kaveh, H.; Moosavi-Zare, A. R.; Hasaninejad, A.; Mokhlesi, M.; Beyzavi, M. H.; Zolfigol, M. A. J. Sulfur Chem. 2012, 33, 259.

[15] Yarahmadi, H.; Shaterian, H. R. J. Chem. Res. 2012, 36, 52.

[16] Shafiee, M. R. M.; Moloudi, R.; Ghashang, M. J. Chem. Res. 2011, 35, 622.

[17] Wang, M.; Wang, Z. C.; Sun, Z. L.; Jiang, H. React. Kinet. Catal. Lett. 2005, 84, 223.

[18] Wang, M.; Wang, Z. C.; Sun, Z. L.; Jiang, H. Transition Met. Chem. 2005, 30, 792.

[19] Wang, M.; Song, Z. G.; Jiang, H. Org. Prep. Proced. Int. 2009, 41, 315.

[20] Wang, M.; Gao, J. J.; Song, Z. G. Z. Naturforsch. 2010, 65b, 1349.

[21] Wang, M.; Song, Z. G.; Gong, H.; Jiang, H. Synth. Commun. 2008, 38, 961.

[22] Wang, M.; Wan, X.; Zhao, S. Indian J. Chem. Technol. 2012, 19, 118.
[23] Ma, J.; Wang, X.-K.; Jiang, H. Chem. Res. Appl. 2004, 16, 789 (in Chinese).
(马杰, 王学凯, 姜恒, 化学研究与应用, 2004, 16, 789.)
Outlines

/