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An eco-benign and high speed protocol for the synthesis of 2-aroyl-3,5-diarylfuran derivatives using Teflon-supported iodine

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Abstract

A new, practical, and convenient approach has been established for the expeditious synthesis of bioactive 2-aroyl-3,5-diarylfurans in excellent yields using a iodine-impregnated Teflon by a microwave-promoted process. The products are isolated without tedious aqueous work-up in high purity. The microwave accelerated the reaction and renders the whole synthesis into a truly eco-friendly protocol.

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References

  1. Barancelli DA, Mantovani AC, Jesse C, Nogueira CW, Zeni G (2009) J Nat Prod 72:857

    Article  CAS  Google Scholar 

  2. Kirsch SF (2006) Org Biomol Chem 4:2076

    Article  CAS  Google Scholar 

  3. Chen K-W, Syu S, Jang Y-J, Lin W (2011) Org Biomol Chem 9:2098

    Article  CAS  Google Scholar 

  4. Reichstein A, Vortherms S, Bannwitz S, Tentrop J, Prinz H, Müller K (2012) J Med Chem 55:7273

    Article  CAS  Google Scholar 

  5. Hou XL, Cheung HY, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HNC (1998) Tetrahedron 54:1955

    Article  CAS  Google Scholar 

  6. Rodríguez A, Moran WJ (2011) Tetrahedron Lett 52:2605

    Article  Google Scholar 

  7. Lutz RE, Reveley WG (1941) J Am Chem Soc 63:3178

    Article  CAS  Google Scholar 

  8. Bello AM, Kotra LP (2003) Tetrahedron Lett 44:9271

    Article  CAS  Google Scholar 

  9. Mortensen DS, Rodriguez AL, Sun J, Katzenellenbogen BS, Katzenellenbogen JA (2001) Bioorg Med Chem Lett 11:2521

    Article  CAS  Google Scholar 

  10. Jiang S, Tala SR, Lu H, Abo-Dya NE, Avan I, Gyanda K, Lu L, Katritzky AR, Debnath AK (2011) J Med Chem 54:572

    Article  CAS  Google Scholar 

  11. Taniguchi T, Nakamura K, Ogasawara K (1997) Synthesis:509

  12. Kinzer GW, Fentiman AI Jr, Page TF, Faltz RL, Vite JP, Pitman GB (1969) Nature 221:477

    Article  CAS  Google Scholar 

  13. Silverstein RM (1981) Science 213:1326

    Article  CAS  Google Scholar 

  14. Oehlschlager AC, Johnston BD (1987) J Org Chem 52:940

    Article  CAS  Google Scholar 

  15. Singh S, Guiry PJ (2009) J Org Chem 74:5758

    Article  CAS  Google Scholar 

  16. Pedersen CL (1975) Acta Chem Scand Ser B 29:791

    Article  Google Scholar 

  17. Li Y, Li Z, Li F, Wang Q, Tao F (2005) Tetrahedron Lett 46:6159

    Article  CAS  Google Scholar 

  18. Chai LT, Li YZ, Wang WW, Wang QR, Tao FG (2007) Chin Chem Lett 18:1460

    Article  CAS  Google Scholar 

  19. Phung T, Zhang Y, Dunlop J, Dalziel J (2011) Biosens Bioelectron 26:3127

    Article  CAS  Google Scholar 

  20. Mouradzadegun A, Dianat S (2009) J Heterocycl Chem 46:778

    Article  CAS  Google Scholar 

  21. Kiasat AR, Mouradzadegun A, Elahi S, Fallah-Mehrjardi M (2010) Chin Chem Lett 21:146

    Article  CAS  Google Scholar 

  22. Mouradzadegun A, Kiasat AR, Kazemian Fard P (2012) Catal Commun 29:1

    Article  CAS  Google Scholar 

  23. Mouradzadegun A, Abadast F (2014) Chem Commun 50:19583

    Article  Google Scholar 

  24. Mouradzadegun A, Abadast F (2013) Tetrahedron Lett 54:2641

    Article  CAS  Google Scholar 

  25. Mouradzadegun A, Abadast F (2013) Monatsh Chem 144:375

    Article  CAS  Google Scholar 

  26. Mouradzadegun A, Abadast F (2014) Synlett 25:448

    Article  CAS  Google Scholar 

  27. Mouradzadegun A, Abadast F (2014) Synth Commun 44:640

    Article  CAS  Google Scholar 

  28. Balaban AT, Dinculescu A, Dorofeenko GN, Fischer GW, Koblik AV, Mezheritskii VV, Schroth W (1982) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 2, suppl 1. Academic Press, New York

    Google Scholar 

  29. Balaban AT, Schroth W, Fischer GW (1969) Pyrylium Salts. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 10. Academic Press, New York, p 241

    Google Scholar 

Download references

Acknowledgements

This work was supported by the Research Council at the University of Shahid Chamran.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran

    Arash Mouradzadegun, Fatemeh Abadast & Fatemeh Rahimi

  2. Center of Excellence in Electrochemistry, University of Tehran, Tehran, Iran

    Arash Mouradzadegun & Mohammad Reza Ganjali

  3. Biosensor Research Center, Endocrinology & Metabolism Molecular-Cellular Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Reza Ganjali

Authors
  1. Arash Mouradzadegun
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  2. Mohammad Reza Ganjali
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  3. Fatemeh Abadast
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  4. Fatemeh Rahimi
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Corresponding author

Correspondence to Arash Mouradzadegun.

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Mouradzadegun, A., Ganjali, M.R., Abadast, F. et al. An eco-benign and high speed protocol for the synthesis of 2-aroyl-3,5-diarylfuran derivatives using Teflon-supported iodine. Monatsh Chem 149, 27–32 (2018). https://doi.org/10.1007/s00706-017-2061-2

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  • DOI: https://doi.org/10.1007/s00706-017-2061-2

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