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An efficient synthesis of furo[3,4-c]coumarins via the reaction of salicylaldehydes, β-ketoesters and isocyanides

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Abstract

A new, practical and efficient method for the synthesis of furo[3,4-c]coumarins via the one-pot reaction of salicylaldehydes, β-ketoesters and isocyanides in the presence of piperidine in toluene has been reported. Reaction of 2-hydroxynaphthalene-1-carboxaldehyde, ethyl acetoacetate and cyclohexyl isocyanide resulted in the formation of benzo[f]furo[3,4-c]coumarin.

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References

  1. P. Lu, Y.G. Wang, Synlett 165 (2010)

  2. B. Ganem, Acc. Chem. Res. 42, 463 (2009)

    Article  CAS  Google Scholar 

  3. A. Dömling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  4. S. Sadjadi, M.M. Heravi, Tetrahedron 67, 2707 (2011)

    Article  CAS  Google Scholar 

  5. R.D.H. Murray, The natural coumarins, occurrence, chemistry and biochemistry (Wiley, New York, 1982)

    Google Scholar 

  6. P.A. Melo, C.L. Ownby, Toxicon 37, 1 (1999)

    Article  Google Scholar 

  7. L. Zhao, R.D. Brinton, J. Med. Chem. 48, 3463 (2005)

    Article  CAS  Google Scholar 

  8. M.D. Mashkovskii, Medicinal preparations (in Russian), Gamta, Vilnius, Vol. 2, 1994

  9. S. Kawaii, Y. Tomono, E. Katase, K. Ogawa, M. Yano, Anticancer Res. 2505 (2000)

  10. R.L. Edelson, J. Photochem. Photobiol. B: Biol. 10, 165 (1991)

    Article  CAS  Google Scholar 

  11. A. Guiotto, A. Chilin, P. Manzini, F. Dall’Aqua, F. Bordin, P. Rodighiero, II Farmaco 50, 479 (1995)

    CAS  Google Scholar 

  12. G. Feuer, in Progress in Medicinal Chemistry, ed. G.P. Ellis, G.B. West, (North Holland Publishing Co., North New York 1974)

  13. A.A. Deana, J. Med. Chem. 26, 580 (1983)

    Article  CAS  Google Scholar 

  14. N. Al-Maharrik, N.P. Botting, Tetrahedron 60, 1637 (2004)

    Article  Google Scholar 

  15. C.C. Li, Z.X. Xie, Y.D. Zhang, J.H. Chen, Z. Yang, J. Org. Chem. 68, 8500 (2003)

    Article  CAS  Google Scholar 

  16. A.J.M. Da Silva, P.A. Melo, N.M.V. Silva, F.V. Broto, C.D. Buarque, D.V. de Souza, V.P. Rodrigues, E.S.C. Pocas, F. Noel, E.X. Albuquerque, P.R.R. Costa, Bioorg. Med. Chem. Lett. 11, 283 (2001)

    Article  Google Scholar 

  17. T. Yao, D. Yue, R.C. Larock, J. Org. Chem. 70, 9985 (2005)

    Article  CAS  Google Scholar 

  18. S. Tollari, G. Palmisano, S. Cenini, G. Cravotto, G.B. Giovenzana, A. Penoni, Synthesis 5, 735 (2001)

    Article  Google Scholar 

  19. K. Kobayashi, K. Sakashita, H. Akamatsu, K. Tanaka, M. Uchida, T. Uneda, T. Kitamura, O. Morikawa, H. Konishi, Heterocycles 51, 2881 (1999)

    Article  CAS  Google Scholar 

  20. G. Cheng, Y.Hu, Chem. Commun. 3285 (2007)

  21. J. Wu, Chem. Lett. 35, 118 (2006)

    Article  CAS  Google Scholar 

  22. L. Zhao, G. Cheng, Y. Hu, Tetrahedron Lett. 49, 7364 (2008)

    Article  CAS  Google Scholar 

  23. D.I. Brahmbhatt, J.M. Gajera, C.N. Patel, V.P. Pandya, U.R. Pandya, J. Heterocycl. Chem. 43, 1699 (2006)

    Article  CAS  Google Scholar 

  24. Y.-J. Jang, S. Syu, Y.-J. Chen, M.-C. Yang, W. Lin, Org. Biomol. Chem. 10, 843 (2012)

    Article  CAS  Google Scholar 

  25. R. Akbarzadeh, P. Mirzaei, A. Bazgir, J. Organomet. Chem. 695, 2320 (2010)

    Article  CAS  Google Scholar 

  26. R. Akbarzadeh, T. Amanpour, P. Mirzaei, A. Bazgir, J. Organomet. Chem. 696, 3421 (2011)

    Article  CAS  Google Scholar 

  27. T. Amanpour, P. Mirzaei, A. Bazgir, Synthesis 44, 235 (2012)

    CAS  Google Scholar 

  28. L.V. Frolova, I. Malik, P.Y. Uglinskii, S. Rogelj, A. Kornienko, I.V. Magedov, Tetrahedron Lett. 52, 6643 (2011)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Imam Khomeini International University, Qazvin, Iran

    Hossein Imanieh & Mansooreh Sarlak

  2. Department of Chemistry, Shahid Beheshti University, General Campus, 1983963113, Tehran, Iran

    Tayebeh Amanpour & Ayoob Bazgir

Authors
  1. Hossein Imanieh
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  2. Mansooreh Sarlak
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  3. Tayebeh Amanpour
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  4. Ayoob Bazgir
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Correspondence to Ayoob Bazgir.

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Imanieh, H., Sarlak, M., Amanpour, T. et al. An efficient synthesis of furo[3,4-c]coumarins via the reaction of salicylaldehydes, β-ketoesters and isocyanides. J IRAN CHEM SOC 10, 851–856 (2013). https://doi.org/10.1007/s13738-013-0220-x

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  • DOI: https://doi.org/10.1007/s13738-013-0220-x

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