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One-pot electrochemical synthesis of highly symmetric and conjugated coumarin derivative

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Abstract

A facile and one pot electrochemical synthesis of disubstituted hydroquinone generated from the electrochemical oxidation of 4-1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone (1) in the presence of 4-hydroxy-6,7-dimethylcoumarin (3) has been reported. The results revealed that p-quinone imine derived from oxidation of (1) participate in Michael addition reactions with 3 and followed by a hydrolysis reaction attain to the highly symmetric and conjugated coumarin derivative. We derived a new product in good yield based on controlled potential electrochemical oxidation at carbon electrode in a divided cell.

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Fig. 1
Scheme 1
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Fig. 4
Scheme 2

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References

  1. S. Palaniappan, R.C. Shekhar, J. Mol. Catal. A: Chem. 209, 117 (2004)

    Article  CAS  Google Scholar 

  2. B. Batanero, M.J. Pe´rez, F. Barba, J. Electroanal. Chem. 469, 201 (1999)

    Article  CAS  Google Scholar 

  3. C.J. Chang, H.G. Floss, J. Org. Chem. 42, 1337 (1977)

    Article  CAS  Google Scholar 

  4. J. D’souza, N. Negaraju, Indian J. Chem. Technol. 15, 244 (2008)

    Google Scholar 

  5. S.L. Zhang, L.K. An, Z.S. Huang, L. Ma, Y.M. Li, A.S.C. Chanc, L.Q. Gu, Tetrahedron 61, 3087 (2005)

    Article  CAS  Google Scholar 

  6. S.L. Zhang, Z.S. Huang, L.K. An, X.Z. Bu, L. Ma, Y.M. Li, A.S.C. Chan, L.Q. Gu, Org. Lett. 6, 4853 (2004)

    Article  CAS  Google Scholar 

  7. N. Vukovic, S. Sukdolak, S. Solujic, N. Niciforovic, Food Chem. 120, 1011 (2010)

    Article  CAS  Google Scholar 

  8. S.M. Golabi, D. Nematollahi, J. Electroanal. Chem. 420, 127 (1997)

    Article  CAS  Google Scholar 

  9. S.M. Golabi, D. Nematollahi, J. Electroanal. Chem. 430, 141 (1997)

    Article  CAS  Google Scholar 

  10. S.L. Zhang, Z.S. Huang, Y.D. Shen, Y.M. Li, J.H. Yao, M. Huang, A.S.C. Chan, L.Q. Gu, Tetrahedron Lett. 47, 6757 (2006)

    Article  CAS  Google Scholar 

  11. S.L. Zhang, Z.S. Huang, L.Q. Gu, Molecules. 14, 1546 (2009)

    Article  CAS  Google Scholar 

  12. D. Nematollahi, A. Amani, J. Electroanal. Chem. 651, 72 (2011)

    Article  CAS  Google Scholar 

  13. D. Nematollahi, A. Amani, J. Electroanal. Chem. 681, 11 (2012)

    Article  Google Scholar 

  14. A.J. Bard, L.R. Faulkner, Electrochemical Methods, 2nd edn. (Wiley, New York, 2001), p. 240

    Google Scholar 

  15. S.S. Hosseiny Davarani, D. Nematollahi, M. Shamsipur, N. Mashkouri Najafi, L. Masoumi, S. Ramyar, J. Org. Chem. 71, 2139 (2006)

    Article  Google Scholar 

  16. R.N. Adams, Electrochemistry at Solid Electrodes. (Marcel Dekker, New York, 1969)

  17. D. Nematollahi, H. Shayani-Jam, M. Alimoradi, S. Niroomand, Electrochim. Acta 54, 7407 (2009)

    Article  CAS  Google Scholar 

  18. D. Nematollahi, A. Amani, Chem. Pharm. Bull. 56, 513 (2008)

    Article  CAS  Google Scholar 

  19. D. Nematollahi, A. Amani, E. Tammari, J. Org. Chem. 72, 3646 (2007)

    Article  CAS  Google Scholar 

  20. S.V. Jovanovic, S. Steenken, C.W. Boone, M.G. Simic, J. Am. Chem. Soc. 121, 9677 (1999)

    Article  CAS  Google Scholar 

  21. CS ChemDraw Professional 15.0, CambridgeSoft Corporation, 100 Cambridge Park Drive, Cambridge, (2003)

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Authors and Affiliations

  1. Department of Medicinal Plants Production, University of Nahavand, Nahavand, Iran

    Ameneh Amani

  2. Faculty of Chemistry, Bu-Ali-Sina University, Hamedan, Iran

    Davood Nematollahi

Authors
  1. Ameneh Amani
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  2. Davood Nematollahi
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Correspondence to Ameneh Amani.

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Amani, A., Nematollahi, D. One-pot electrochemical synthesis of highly symmetric and conjugated coumarin derivative. J IRAN CHEM SOC 15, 2669–2674 (2018). https://doi.org/10.1007/s13738-018-1455-3

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  • DOI: https://doi.org/10.1007/s13738-018-1455-3

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