Advertisement

Research on Chemical Intermediates

, Volume 39, Issue 4, pp 1745–1751 | Cite as

Synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones catalyzed by biodegradable ionic liquid

  • Dong Fang
  • Jin-ming Yang
  • Yan-fang Cao
Article

Abstract

A biodegradable acyclic SO3H-functionalized ionic liquid has been used as a novel catalyst for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones via one-pot multi-component condensation of β-naphthol, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds, under solvent-free conditions, to afford good to excellent yields ranging from 85 to 93 % within 30–60 min. After the reaction the products could be simply separated from the reaction mixture and the catalyst could be recycled and reused several times without noticeable reduction of catalytic activity.

Graphical Abstract

Keywords

Xanthene Synthesis Biodegradable ionic liquid Solvent-free Multi-component reaction 

Notes

Acknowledgments

We express our sincere thanks to the Ministry of Science and Technology of the P.R. China (11C26213201395), Jiangsu Provincial Department of Education (JHB2011-52), and the Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1112) for financial assistance.

References

  1. 1.
    J.M. Jamison, K. Krabill, A. Hatwalkar, Cell Biol. Int. Rep. 14, 1075 (1990)CrossRefGoogle Scholar
  2. 2.
    K. Chibale, M. Visser, D.V. Schalkwyk, P.J. Smith, A. Saravanamuthu, A.H. Fairlamb, Tetrahedron 59, 2289 (2003)CrossRefGoogle Scholar
  3. 3.
    B.B. Bhowmik, P. Ganguly, Spectrochim. Acta A 61, 1997 (2005)CrossRefGoogle Scholar
  4. 4.
    C.G. Knight, T. Stephens, Biochem. J. 258, 683 (1989)Google Scholar
  5. 5.
    M. Ahmad, T.A. King, B.H. Cha, J. Lee, J. Phys. D Appl. Phys. 35, 1473 (2002)CrossRefGoogle Scholar
  6. 6.
    C.S. Sundar, K.U.M. Rao, N.B. Reddy, M.V.N. Reddy, S.S. Prasad, C.S. Reddy, Catal. Sci. Technol. (2012). doi: 10.1039/c2cy20041d
  7. 7.
    A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem. 12, 20 (2010)CrossRefGoogle Scholar
  8. 8.
    G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65, 7129 (2009)CrossRefGoogle Scholar
  9. 9.
    B. Das, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, Synlett 20, 3107 (2007)CrossRefGoogle Scholar
  10. 10.
    J.J. Li, W.Y. Tang, L.M. Lu, W.K. Su, Tetrahedron Lett. 49, 7117 (2008)CrossRefGoogle Scholar
  11. 11.
    R.Z. Wang, L.F. Zhang, Z.S. Cui, Synth. Commun. 39, 2101 (2009)CrossRefGoogle Scholar
  12. 12.
    J.J. Li, L.M. Lu, W.K. Su, Tetrahedron Lett. 51, 2434 (2010)CrossRefGoogle Scholar
  13. 13.
    J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 4777 (2009)CrossRefGoogle Scholar
  14. 14.
    N. Karimi, H.A. Oskooie, M.M. Heravi, L. Tahershamsi, Synth. Commun. 41, 307 (2011)CrossRefGoogle Scholar
  15. 15.
    Z.H. Zhang, P. Zhanz, S.H. Yang, H.J. Wang, J. Deng, J. Chem. Sci. 122, 427 (2010)CrossRefGoogle Scholar
  16. 16.
    S. Sudha, M.A. Pasha, Ultrason. Sonochem. 19, 994 (2012)CrossRefGoogle Scholar
  17. 17.
    A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, A. Khalafi-Nezhad, Catal. Commun. 20, 54 (2012)CrossRefGoogle Scholar
  18. 18.
    C.B. Yue, T.F. Yi, C.B. Zhu, G. Liu, J. Ind. Eng. Chem. 15, 653 (2009)CrossRefGoogle Scholar
  19. 19.
    W. Chen, H. Yin, Y. Zhang, Z. Lu, A. Wang, Y. Shen, T. Jiang, L. Yu, J. Ind. Eng. Chem. 16, 800 (2010)CrossRefGoogle Scholar
  20. 20.
    Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 14, 201 (2012)CrossRefGoogle Scholar
  21. 21.
    D. Fang, S.T. Cao, Z.H. Fei, Z.L. Liu, Chin. J. Energ. Mater. 17, 404 (2009)Google Scholar
  22. 22.
    D. Fang, C.M. Jiao, H.B. Zhang, J. Ind. Eng. Chem. 16, 233 (2010)CrossRefGoogle Scholar
  23. 23.
    D. Fang, J.M. Yang, C.M. Jiao, Catal. Sci. Technol. 1, 243 (2011)CrossRefGoogle Scholar
  24. 24.
    A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes Jr, J.H. Davis, J. Am. Chem. Soc. 124, 5962 (2002)CrossRefGoogle Scholar
  25. 25.
    J. Shen, H. Wang, H. Lium, Y. Sun, Z. Liu, J. Mol. Catal. A: Chem. 280, 24 (2007)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  1. 1.Department of Pharmaceutical EngineeringYancheng Normal UniversityJiangsuPeople’s Republic of China

Personalised recommendations