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NaI readily mediated oxidative aromatization of Hantzsch 1,4-dihydropyridines with hydrogen peroxide at room temperature: A green procedure

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Abstract

The oxidative conversion of 1,4-dihydropyridines to give the corresponding pyridine derivatives in excellent yields was easily effected using the catalytic amount of NaI in combination with H2O2 (30%) as a green external oxidant. The process is highly green wherein the solid products are easily filtered out after the addition of ice-water to the reaction mixture. This non-transition metal catalyst is cost-effective, affords simple work-up and easy separation of the product.

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References

  1. G.W. Zamponi, S.C. Stotz, R.J. Staples, T.M. Andro, J.K. Nelson, V. Hulubei, A. Blumenfeld, N.R. Natale, J. Med. Chem. 46 (2003) 87

    CAS  Google Scholar 

  2. S. Visentin, B. Rolando, A. Di Stilo, R. Frutterro, M. Novara, E. Carbone, C. Roussel, N. Vanthuyne, A. Gasco, J. Med. Chem. 47 (2004) 2688

    CAS  Google Scholar 

  3. A. Zarghi, H. Sadeghi, A. Fassihi, M. Faizi, A. Shafiee, Farmaco. 58 (2003) 1077

    CAS  Google Scholar 

  4. R. Peri, S. Padmanabhan, A. Rutledge, S. Singh, D.J. Triggle, J. Med. Chem. 43 (2000) 2906.

    CAS  Google Scholar 

  5. P.S. Kharkar, B. Desai, H. Gaveria, B. Varu, R. Loriya, Y. Naliapara, A. Shah, V.M. Kulkarn, J. Med. Chem. 45 (2002) 4858.

    CAS  Google Scholar 

  6. T. Tsuruo, H. Iida, M. Nojiri, S. Tsukagoshi, Y. Sakurai, Cancer Res. 43 (1983) 2905.

    CAS  Google Scholar 

  7. R.W. Chapman, G. Danko, M.I. Siegels, Pharmacology 29 (1984) 282.

    CAS  Google Scholar 

  8. W.J. Malaise, P.C.F. Mathias, Diabetologia 28 (1985) 153.

    Google Scholar 

  9. A. Krauze, S. Germane, O. Eberlins, I. Sturms, V. Klusa, G. Duburs, Eur. J. Med. Chem. 34 (1999) 301.

    CAS  Google Scholar 

  10. R. Peri, S. Padmanabhan, S. Singh, A. Rutledge, D.J. Triggle, J. Med. Chem. 43 (2000) 2906.

    CAS  Google Scholar 

  11. G.S. Poindexter, M.A. Bruce, J.G. Breitenbucher, M.A. Higgins, S.-Y. Sit, J.L. Romine, S.W. Martin, S.A. Ward, R.T. McGovern, W. Clarke, J. Russell, I. Antal-Zimanyi, Bioorg. Med. Chem. 12 (2004) 507

    CAS  Google Scholar 

  12. G.S. Poinder, M.A. Bruce, K.L. LeBoulluec, I. Monkovic, S.W. Martin, E.M. Parker, L.G. Iben, R.T. McGovem, A.A. Ortiz, J.A. Stanley, G.K. Mattson, M. Kozlowski, M. Arcuri, I.A. Zimanyi, Bioorg. Med. Chem. Lett. 12 (2002) 379.

    Google Scholar 

  13. R.J. Kill, D.A. Widdowson, In Bioorganic Chemistry, Vol. 4, Academic Press, New York, 1978, p. 239.

    Google Scholar 

  14. B. Khadikar, S. Borkat, Synth. Commun. 28 (1998) 207.

    Google Scholar 

  15. M.A. Zolfigol, M. Safaiee, Synlett. (2004) 827

    Google Scholar 

  16. B. Loev, M.M. Goodman, K.M. Snader, R. Tedeschi, E. Macko, J. Med. Chem. 19 (1974) 956

    Google Scholar 

  17. M. Moghadam, M. Nasr-Esfahani, S. Tangestaninejad, V. Mirkhani, Bioorg. Med. Chem. Lett. 16 (2006) 2026

    CAS  Google Scholar 

  18. M. Moghadam, M. Nasr-Esfahani, S. Tangestaninejad, V. Mirkhani, Bioorg. Med. Chem. Lett. 15 (2005) 3276

    Google Scholar 

  19. M.M. Heravi, F. Derikvand, S. Hassan-Pour, K. Bakhtiari, F.F. Bamoharram, H.A. Oskooie, Bioorg. Med. Chem. Lett. 17 (2007) 3305

    CAS  Google Scholar 

  20. J. Arguello, L.J. Núñez-Vergara, J.C. Sturm, J.A. Quella, Electrochimica Acta 49 (2004) 4849

    CAS  Google Scholar 

  21. B. Han, Z. Liu, Q. Liu, L. Yang, Z.L. Liu, W. Yu, Tetrahedron 62 (2006) 2492

    CAS  Google Scholar 

  22. H. Adibi, A.R. Hajipour, Bioorg. Med. Chem. Lett. 17 (2007) 1008

    CAS  Google Scholar 

  23. M. Filipan-Litvic, M. Litvic, V. Vinkovic, Bioorg. Med. Chem. Lett. 16 (2008) 9276

    CAS  Google Scholar 

  24. M. Filipan-Litvic, M. Litvic, V. Vinkovic, Tetrahedron 64 (2008) 10912

    CAS  Google Scholar 

  25. L.J. Peng, J.T. Wang, Z. Lu, Z.Q. Lu, U.M. Wu, Tetrahedron Lett. 49 (2008) 1586

    CAS  Google Scholar 

  26. E. Fasani, A. Albini, M. Mella, Tetrahedron 64 (2008) 3190

    CAS  Google Scholar 

  27. M. Anniyappan, D. Muralidharan, P.T. Perumal, Tetrahedron 58 (2002) 5069

    CAS  Google Scholar 

  28. B. Zeynizadeh, K. Akbari, A. Roozijoy, J. Chin. Chem. Soc. 52 (2005) 1001

    CAS  Google Scholar 

  29. M. Filipan-Litvic, M. Litvic, V. Vinkovic, Arkivoc (2008) 96

    Google Scholar 

  30. H.R. Memarian, M. Javahery, J. Chin. Chem. Soc. 53 (2006) 511

    CAS  Google Scholar 

  31. S. Paul, S. Sharma, M. Gupta, R. Gupta, D. Choudhary, Bull. Korean Chem. Soc. 28 (2007) 2

    Google Scholar 

  32. C. Xiao-Hua, Y. Hai-Jun, Z. Guo-Lin, Can. J. Chem. 83 (2005) 273

    Google Scholar 

  33. M.M. Hashemi, Y. Ahmadi, H. Ghafuri, Monatshefte fur Chemie. 134 (2003) 107.

    CAS  Google Scholar 

  34. M. Balogh, I. Hermecz, Z. Meszaros, P. Laszlo, Helv. Chim. Acta 67 (1984) 2270.

    CAS  Google Scholar 

  35. W.J. Craig, Applications of Hydrogen Peroxide and Derivatives, The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road Cambridge CB4 OWF, UK, 1999.

    Google Scholar 

  36. M.M. Hashemi, Y. Ahmadibeni, H. Ghafuri, Monatsh. Chem. 134 (2003) 107

    CAS  Google Scholar 

  37. A.R. Momeni, H. Aliyan, H. Mombeini, Z. Naturforsch, Chem. Sci. 61 (2006) 331

    CAS  Google Scholar 

  38. M.F. Litvic, M. Litvic, V. Vinkovic, Tetrahedron 64 (2008) 5649.

    Google Scholar 

  39. A.A. Jafari, F. Moradgholi, F. Tamaddon, Eur. J. Org. Chem. (2009) 12495

    Google Scholar 

  40. A.A. Jafari, F. Moradgholi, F. Tamaddon, J. Iran. Chem. Soc. 6 (2009) 588

    Article  CAS  Google Scholar 

  41. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 347 (2005) 655

    CAS  Google Scholar 

  42. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 348 (2006) 434.

    CAS  Google Scholar 

  43. F. Tamaddon, Z. Razmi, A.A. Jafari, Tetrahedron Lett. 51 (2010) 1187.

    CAS  Google Scholar 

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Correspondence to M. A. Amrollahi.

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Shahabi, D., Amrollahi, M.A. & Jafari, A.A. NaI readily mediated oxidative aromatization of Hantzsch 1,4-dihydropyridines with hydrogen peroxide at room temperature: A green procedure. JICS 8, 1052–1057 (2011). https://doi.org/10.1007/BF03246562

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