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An improved, safe, and efficient conversion of triarylpyrylium perchlorates to corresponding cyanodienones using Amberlite IRA 910[CN]

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Abstract

Triarylpyrylium perchlorates are readily converted into new aromatic cyanodienones by using cyanide impregnated on anion exchange resin as a safe and efficient reagent.

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References

  1. Villemin D, Cheikh N, Mostefa-Kara B, Bar N, Choukchou-Braham N, Didi MA (2006) Tetrahedron Lett 47:5519

    Article  CAS  Google Scholar 

  2. Karade NN, Gampawar SV, Kondre JM, Shinde SV (2008) Tetrahedron Lett 49:4402

    Article  CAS  Google Scholar 

  3. De Rosa M, Citro L, Soriente A (2006) Tetrahedron Lett 47:8507

    Article  Google Scholar 

  4. Fakova H, Pour M, Kunes J, Senel P (2005) Tetrahedron Lett 46:8137

    Article  CAS  Google Scholar 

  5. Sabitha G, Prasad MN, Ramesh M, Yadav JS (2010) Monatsh Chem 141:1245

    Article  CAS  Google Scholar 

  6. Renard M, Ghosez LA (2001) Tetrahedron 57:2597

    Article  CAS  Google Scholar 

  7. Harris LJ, Alexander NJ, Saparno A, Blackwell B, McCormick SP, Desjardins AE, Robert LS, Tinker N, Hattori J, Piché C, Schernthaner JP, Watson R, Ouellet T (2007) Fungal Genet Biol 44:293

    Article  CAS  Google Scholar 

  8. Burger K, Hennig L, Fuchs A, Greif D, Spengler J, Albericio F (2005) Monatsh Chem 136:1763

    Article  CAS  Google Scholar 

  9. Suzuki Y, Nishimaki R, Ishikawa M, Murata T, Takao K, Tadano K (2000) J Org Chem 65:8595

    Article  CAS  Google Scholar 

  10. Fan WY, Wang ZL, Zhang ZG, Li HC, Deng WP (2011) Tetrahedron 67:5596

    Article  CAS  Google Scholar 

  11. Lipka E, Vaccher MP, Vaccher C, Lens C (2005) Bioorg Med Chem Lett 15:501

    Article  CAS  Google Scholar 

  12. Len C, Selouane A, Weilling A, Coicon F, Postel D (2003) Tetrahedron Lett 44:663

    Article  CAS  Google Scholar 

  13. Balaban AT, Nenitzescu CD (1961) J Chem Soc 3566

  14. Balaban AT, Tudose A, Caproiu MT (2003) Tetrahedron 59:3291

    Article  CAS  Google Scholar 

  15. Balaban AT, Silhan W (1970) Tetrahedron 26:743

    Article  CAS  Google Scholar 

  16. Mouradzadegun A, Gheitasvand N (2005) Phosphorus Sulfur Silicon 180:1385

    Article  CAS  Google Scholar 

  17. Ganjali MR, Norouzi P, Emami M, Golmohamadi M, Pirelahi H, Mouradzadegun A (2006) J Chin Chem Soc 53:1209

    CAS  Google Scholar 

  18. Ganjali MR, Akbar V, Daftari A, Norouzi P, Pirelahi H, Mouradzadegun A (2004) J Chin Chem Soc 51:309

    CAS  Google Scholar 

  19. Mouradzadegun A, Pirelahi H (2001) J Photochem Photobiol A Chem 138:203

    Article  CAS  Google Scholar 

  20. Mouradzadegun A, Pirelahi H (2000) Phosphorus Sulfur Silicon 165:149

    Article  CAS  Google Scholar 

  21. Mouradzadegun A, Pirelahi H (2000) Phosphorus Sulfur Silicon 157:193

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. Mouradzadegun A, Ghasem Hezave F, Karimnia M (2010) Phosphorus Sulfur Silicon 185:84

    Article  CAS  Google Scholar 

  24. Ortega MJ, Zubia E, Ocana JM, Naranjo S, Salva J (2000) Tetrahedron 56:3963

    Article  CAS  Google Scholar 

  25. Clark B, Capon RJ, Lacey E, Tennant S, Gill JH, Bulheller B, Bringmann G (2005) J Nat Prod 68:1226

    Article  CAS  Google Scholar 

  26. Bellina F, Anselmi C, Viel S, Mannina L, Rossi R (2001) Tetrahedron 57:9997

    Article  CAS  Google Scholar 

  27. Ma S, Shi Z, Wu S (2001) Tetrahedron Asymmetry 12:193

    Article  CAS  Google Scholar 

  28. Wu J, Zhu Q, Wang L, Fathi R, Yang Z (2003) J Org Chem 68:670

    Article  CAS  Google Scholar 

  29. Kim YH, Hong JI (2002) Chem Commun 512

  30. Tomasulo M, Sortino S, White AJP, Raymo FM (2006) J Org Chem 71:744

    Article  CAS  Google Scholar 

  31. Lee KS, Kim HJ, Kim GH, Shin I, Hong JI (2008) Org Lett 10:49

    Article  CAS  Google Scholar 

  32. Castrica L, Fringuelli F, Gregoli L, Pizzo F, Vaccaro L (2006) J Org Chem 71:9536

    Article  CAS  Google Scholar 

  33. Niknam K, Kiasat AR, Karimi S (2005) Synth Commun 35:2231

    Article  CAS  Google Scholar 

  34. Praharaj S, Nath S, Ghosh SK, Kundu S, Pal T (2004) Langmuir 20:9889

    Article  CAS  Google Scholar 

  35. Druschel GK, Schoonen MA, Nordstrom DK, Ball JW, Xu Y, Cohn CA (2003) Geochem Trans 4:12

    Article  Google Scholar 

  36. Tamami B, Iranpoor N, Rezaei R (2003) Synth Commun 33:3153

    Article  CAS  Google Scholar 

  37. 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, New York

    Google Scholar 

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

    Google Scholar 

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Acknowledgments

This work was supported by the Research Council at the University of Shahid Chamran. Thanks are expressed to Mr. A.T. Balaban for providing some references.

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Authors and Affiliations

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

    Arash Mouradzadegun & Fatemeh Abadast

Authors
  1. Arash Mouradzadegun
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  2. Fatemeh Abadast
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Correspondence to Arash Mouradzadegun.

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Mouradzadegun, A., Abadast, F. An improved, safe, and efficient conversion of triarylpyrylium perchlorates to corresponding cyanodienones using Amberlite IRA 910[CN]. Monatsh Chem 144, 375–379 (2013). https://doi.org/10.1007/s00706-012-0825-2

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  • DOI: https://doi.org/10.1007/s00706-012-0825-2

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