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Microwave-assisted, methanesulfonic acid-catalyzed synthesis of 3,3′-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones)

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Abstract

Efficient synthesis of 3,3′-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones) has been achieved by methanesulfonic acid-catalyzed, microwave-assisted reaction of 4-hydroxycoumarin and aromatic aldehydes in ethanol. The procedure has the advantages of high yield, short reaction time, low energy consumption, and convenient work-up. Compound structures were confirmed by IR, 1H NMR, and 13C NMR spectroscopy and by elemental analysis.

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References

  1. J.H. Lee, H.B. Bang, S.Y. Han et al., Tetrahedron Lett. 48, 2889 (2007)

    Article  CAS  Google Scholar 

  2. R.D.R.S. Manian, J. Jayashankaran, R. Raghunathan, Tetrahedron Lett. 48, 1385 (2007)

    Article  CAS  Google Scholar 

  3. H. Zhao, N. Neamati, H. Hong et al., J. Med. Chem. 40, 242 (1997)

    Article  CAS  Google Scholar 

  4. G.K. Maria, E.J. Marian, Med. Pharm. Chem. 3, 583 (1961)

    Article  Google Scholar 

  5. I. Kostova, N. Trendafilova, G.J. Momekov, Inorg. Biochem. 99, 477 (2005)

    Article  CAS  Google Scholar 

  6. M. Ilia, M.M. Caecilia, D. Nicolay, Eur. J. Med. Chem. 41, 882 (2006)

    Article  Google Scholar 

  7. I.I. Manolov, Tetrahedron Lett. 39, 3041 (1998)

    Article  CAS  Google Scholar 

  8. P.C.M. Mao, J.F. Mouscadet et al., Chem. Pharm. Bull. 50(12), 1634 (2002)

    Article  CAS  Google Scholar 

  9. C.X. Su, J.F. Mouscadet, C.C. Chiang et al., Chem. Pharm. Bull. 54, 682 (2006)

    Article  CAS  Google Scholar 

  10. J. Wang, D.Q. Shi, Q.Y. Zhuang et al., Chin. J. Org. Chem. 25, 926 (2005)

    CAS  Google Scholar 

  11. K. Mazaahir, V. Bansal, P. Mothsra et al., J. Mol. Catal. A: Chem. 268, 76 (2007)

    Article  Google Scholar 

  12. A. Khodabocus, B.M.P. Beebeejaun, Sci. Technol. 5, 21 (2000)

    Google Scholar 

  13. M. Wang, Y. Liang, T. Zhang et al., Chin. J. Chem. 29, 1656 (2011)

    Article  CAS  Google Scholar 

  14. V. Premasagar, V.A. Palaniswamy, E.J.J. Eisenbraun, Org. Chem. 46, 2974 (1981)

    Article  CAS  Google Scholar 

  15. D. Kumar, S. Rudrawar, A.K. Chakraborti, Austr. J. of Chem. 61, 881 (2008)

    Article  CAS  Google Scholar 

  16. Shen, Y. B. and Wang, G. W. ARKIVOC. (xvi), 1 (2008)

  17. S.J. Tu, C.M. Li, G.G. Li et al., J. Comb. Chem. 9, 1144 (2007)

    Article  CAS  Google Scholar 

  18. J.F. Zhou, G.X. Gong, K.B. Shi et al., Chin. Chem. Lett. 20, 672 (2009)

    Article  CAS  Google Scholar 

  19. J.F. Zhou, G.X. Gong, H.Q. Zhu et al., Chin. Chem. Lett. 20, 1198 (2009)

    Article  CAS  Google Scholar 

  20. J. Wang, S. Cheng, C.F. Gong et al., Chin. J. Chem. 29, 2101 (2011)

    Article  CAS  Google Scholar 

  21. G.X. Gong, L.T. An et al., Chin. J. Org. Chem. 29, 1988 (2009)

    Google Scholar 

  22. Zhou, J. F.; Sun, X.J.; Lou, F. W. et al., Res Chem Intermed. 38, (2012). doi:10.1007/s11164-012-0696-5

  23. M. Kidwai, V. Bansal, P. Mothsra et al., J. Mol. Catal. A: Chem. 268, 76 (2007)

    Article  CAS  Google Scholar 

  24. J. Wang, D.Q. Shi, Q.Y. Zhuang et al., Chin. J. Org. Chem. 25, 926 (2005)

    CAS  Google Scholar 

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Correspondence to Jian-Feng Zhou.

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Qi, X., Xue, MW., Sun, XJ. et al. Microwave-assisted, methanesulfonic acid-catalyzed synthesis of 3,3′-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones). Res Chem Intermed 40, 1187–1192 (2014). https://doi.org/10.1007/s11164-013-1031-5

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  • DOI: https://doi.org/10.1007/s11164-013-1031-5

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