One-pot synthesis of bis-(4-hydroxycoumarin-3-yl)-methanes using nano α-Al2O3/MoO3 in water

Document Type : Original Article

Abstract

A green, simple and efficient procedure has been developed using nano α-Al2O3/MoO3 as a heterogeneous catalyst for the synthesis of bis-(4-hydroxycoumarin-3-yl)-methanes via the condensation of 4-hydroxycoumarin with aldehydes in water. High yields, short reaction times, no chromatographic separation, and recyclability of the catalyst are the advantages of this procedure.

Keywords


  1. B. Maleki, S. Barzegar, Z. Sepehr, M. Kermanian, R. Tayebee, J. Iran. Chem. Soc. 9 (2012) 757.
  2. R. Tayebee, B. Maleki, M. Ghadamgahi, Chin. J. Catal. 33 (2012) 659.
  3. N. Koukabi, S. Otokesh, A. Amoozadeh, E. Kolvari, J. Appl. Chem. 9 (2014) 31.
  4. B. Maleki, S. Sedigh Ashrafi, RSC Adv. 4(2014)42873.
  5. R. D. H. Murray, J. Medez, S. A. Brown, The natura, coumarins: Occurrence, Chemistry and Biochemistry. Willey. 1982.
  6. M. I. Choudhary, N. Fatima, K. M. Khan, S. Jalil, S. Igbal, A. Rahman, Bioorg. Med. Chem. 14 (2006) 8066.
  7. C. X. Su, J. F. Mouscadet, C. C. Chiang, H. J. Tsai, L. Y. Hsu, Chem. Pharm. Bull. 54 (2006) 682.
  8. S. S. Li, Z. Gao, X. Feng, S. M. Hecht, J. Nat. Prod. 67 (2004) 1608.
  9. B. Y. Park, B. S. Min, S. R. Oh, J. H. Kim, K. H. Bae, K. H. Lee, Phytother. Res. 67 (2006) 1608.
  10. F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Curr. Med. Chem. 12 (2005) 887.
  11. R. S. Sheelavantar, G. N. Alawandi, M. V. Kulkarni, Proc. Natl. Acad. Sci. Ind. Phys. Sci. 74 (2004) 87.
  12. A. Romeo, M. Prosdocimi, Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters. Patent no. WO 9222545. 1992.
  13. I. Manolov, C. Maichle-Moessmer, I. Nicolova, N. Danchev, Arch. Pharm. 339 (2006) 319.
  14. M. Mercep, I. Malvar, B. Hrvacic, S. Markovic, A. Filipovic-Sucic, B. Bosnjak, A. Cempuh-Klonkay, R. Rupcic, A. Hutinec, I. J. Elenkov, M. Mesic, Synthesis and spectroscopic study of new biscoumarindyes based on 7-(4-methylcoumarinyl) diesters. Patent no. WO 2006111858. 2006.
  15. M. V. R. Reddy, R. E. Premkumar, Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters. Patent no. WO 2006132947. 2006.
  16. I. Kostova, G. Momekov, Eur. J. Med. Chem. 41 (2006) 717.
  17. I. Kostova, G. Momekov, M. Zaharieva, M. Karaivanova, Eur. J. Med. Chem. 40 (2005) 542.
  18. R. T. Kuznetsova, N. S. Savenkova, T. N. Kopylova, A. V. Reznichenko, M. A. A. Tavrizova, High Energy Chem. 37 (2003) 246.
  19. E. G. Tsatsaroni, S. M. Lin, A. T. Peters, J. SOC. Dyers. Col. 115 (1999) 62.
  20. M. M. Asimov, V. M. Nikitchenko, A. I. Nivikon, A. N. Rubinov, Z. Bor, L. Gaty, Chem. Phys. Lett. 149 (1988) 140.
  21. M. R. Padhey, T. S. Varadarajan, A. V. Deshpande, Spect. Lett. 17 (1984) 369.
  22. A. Ootsuji, R. Suzuki, T. Uragami, H. Takuma, Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters. Patent no. JP 09208574. 1997.
  23. G. Appendino, G. Cravotto, S. Tagliaoietra, S. Ferraro, G. M. Nano, G.  Palmisano, Helv. Chim. Acta. 74 (1991) 1451.
  24. M. A .Zolfigol, A. R. Moosavi-Zare, M. Zarei, C. R. Chim. 17 (2014) 1264.
  25. R. Rezaei, F. Moezzi, M. M. Doroodmand, Chin. Chem. Lett. 25 (2014) 183.
  26. F. Shirini, M. Abedini, S. Abroon Kiaroudi, Phosphorus, Sulfur, and Silicon, 189 (2014) 1279.
  27. A. R. Kiasat, L. Hemat-Alian, Res. Chem. Intermed. 41 (2015) 873.
  28. S. C. Azimi, K. Rad-Moghadam, Iran. Chem. Commun. 3 (2015) 356.
  29. R. Rezaei, M. R. Sheikhi, Res. Chem. Intermed. 41 (2015) 1283.
  30. Jalal Albadi, Azam Mansournezhad, Sara Salehnasab, Res. Chem. Intermed. 41 (2015) 5713.
  31. K. Parvanak Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh Chem. 145 (2014) 1023.
  32. W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141 (2011) 1651.
  33. B. Maleki, Org. Prep. Proced. Int. 48 (2016) 303.
  34. F. Barath, M. Turki, V. Keller, G. Maire, J. Catal. 185 (1999) 1.
  35. B. Maleki, H. Eshghi, A. Khojastehnezhad, R. Tayebee, S. Sedigh Ashrafi, G. Esmailian Kahoo, F. Moeinpour, RSC Adv. 5 (2015) 64850.
  36. B. Maleki, E. Rezaei-Seresht, Z. Ebrahimi, Org. Prep. Proced. Int. 47 (2015) 149.
  37. B. Maleki, A. Davoodi, M. Vakili Azghandi, M. Baghayeri, E. Akbarzadeh, H. Veisi, S. Sedigh Ashrafi, M. Raei, New J. Chem. 40(2016)1278.
  38. B. Maleki,S. Barat Nam Chalaki, S. Sedigh Ashrafi, E. Rezaei Seresht, F. Moeinpour, A. Khojastehnezhad, R. Tayebee, Appl. Organomet. Chem. 29 (2015) 290.
  39. B. Maleki, S. Sedigh Ashrafi, R. Tayebee, RSC Adv., 4 (2014) 41521.
  40. B. Maleki, F. Taimazi, Org. Prep. Proced. Int. 46 (2014) 252.
  41. B. Maleki H. Veisi, Bull. Korean Chem. Soc. 32 (2011) 4367.
  42. B. Maleki, Org. Prep. Proced. Int. 47 (2015) 173.
  43. B. Maleki, S. Shiekh, RSC Adv. 5 (2015) 42997.
  44. B. Maleki, F. Mohammadi Zonoz, H. A. Akhlaghi, Org. Prep. Proced. Int. 47 (2015) 361.
  45. R. Tayebee, M. Jarrahi, B. Maleki, M. K. Razi, Z. B. Mokhtari, S. M. Baghbanian, RSC Adv. 5 (2015) 10869.
  46. B. Maleki, M. Raei, E. Akbarzadeh, H. Ghasemnejad-Bosra, A. R. Sedrpoushan, S. Sedigh Ashrafi,M. Nabi Dehdashti, Org. Prep. Proced. Int. 48 (2016) 62.
  47. B. Maleki, M. Baghayeri, J. Baedi, S. Sedigh Ashrafi, J. Appl. Chem. 11 (2016) 107.
  48. B. Maleki, E. Akbarzadeh, S. Babaee. Dyes Pigmet. 123 (2015) 222.
  49. B. Maleki, Org. Prep. Proced. Int. 48 (2016) 81.
  50. M. Bitaraf, A. Amoozadeh, J. Appl. Chem. 10 (2014) 109.
  51. E. Kolvari, A. Amoozadeh, S. Azhari, S. Otokesh, J. Appl. Chem. 9 (2014) 79.
  52. B. Maleki,G. Esmailian Kahoo, R. Tayebee, Org. Prep. Proced. Int. 47 (2015) 461.
  53. B. Maleki,E. Sheikh,E. Rezaei-Seresht,H. Eshghi, S. Sedigh Ashrafi, A. Khojastehnezhad, H. Veisi, Org. Prep. Proced. Int. 48 (2016) 37.
  54. E. Tabrizian, A. Amoozadeh, J. Appl. Chem. 9 (2014) 23.
  55. B. Maleki, S. Babaee, R. Tayebee, Appl. Organomet. Chem. 29 (2015) 408.
  56. C. J. Li, Chem. Rev. 105 (2005) 3095.
  57. B. Maleki, M. Baghayeri, S. M. Vahdat, A. Mohammadzadeh, S. Akhoondi, RSC Adv. 5 (2015) 46545.
  58. H. Veisi, P. Mohammadi, J. Gholami, Appl. Organomet. Chem. 28 (2014)868.

H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, M. Haji Aliani, T. Ozturk, Appl. Organomet. Chem. 29 (2015) 26