JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 66 No 2 (2021): Journal of the Chilean Chemical Society
Original Research Papers

Ag/CuO/MCM-48 AS A POTENTIAL CATALYST FOR THE SYNTHESIS OF SYMMETRICAL AND UNSYMMETRICAL POLYHYDROQUINOLINES

Narges Vahdati
University of Guilan
Bio
Manouchehr Mamaghani
University of Guilan
Behzad Khalili
University of Guilan
Bio
Fateme Tavakoli
University of Guilan
Bio
Published June 12, 2021
Keywords
  • Ag/CuO/MCM-48,
  • Multicomponents reaction,
  • One-pot synthesis,
  • Polyhydroquinoline
How to Cite
Vahdati, N., Mamaghani, M., Khalili, B., & Tavakoli, F. (2021). Ag/CuO/MCM-48 AS A POTENTIAL CATALYST FOR THE SYNTHESIS OF SYMMETRICAL AND UNSYMMETRICAL POLYHYDROQUINOLINES . Journal of the Chilean Chemical Society, 66(2), 5136-5141. Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/1588

Abstract

Ag/CuO/MCM-48 as a heterogeneous catalyst was efficiently employed in the synthesis of diversely substituted symmetrical and unsymmetrical polyhydroquinoline by a multi-component reaction of arylaldehyde, dimedone, ethyl cyanoacetate and ammonium acetate. This novel method is simple, environmentally friendly, rapid, use a recyclable catalyst and produce the products in high to excellent yields (83-97%) and lower reaction times (17-35 min). The catalyst can be reused at least 10 times without any appreciable decrease in its catalytic activities.

15881.jpg

References

  1. - F. Bossert, H. Meyer, E. Wehinger, Angew. Chem., Int. Ed. Engl. 20, 762, (1981)
  2. - H. Nakayama, Y. Kasoaka, Heterocycles 42, 901, (1996)
  3. - T. Godfraid, R. Miller , M. Wibo, Pharmocol. Rev. 38, 321, (1986)
  4. - R. G. Bretzel, C. C. Bollen, E. Maester, K. F. Federlin, Drugs Future 17, 465, (1992)
  5. - P. N. Kalaria, S. P. Satasia, D. K. Raval, Eur. J. Med. Chem. 78, 207, (2014)
  6. - G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. MaCarthy, R. Zhang , S. Mereland, J. Med. Chem. 38, 119, (1995)
  7. - C. O. Kappe, W. M. F. Fabian, M. A. Semones, Tetrahedron 53, 2803, (1997)
  8. - K. Aouam , A. Berdeaux, Therapie 58, 333, (2003)
  9. - A. Hilgeroth, Mini-Rev. Med. Chem. 2, 235, (2002)
  10. - U. Eisner, J. Kuthan, Chem. Rev. 72, 1, (1972)
  11. - D. M. Stout, A. I. Meyers, Chem. Rev. 82, 223, (1982)
  12. - A. Sausins, G. Duburs, Heterocycles 27, 269, (1988)
  13. - N. Koukabi, E. Kolvari, A. Khazaei, M. A. Zolfigol, B. S. Shaghasemi, H. R. Khavasi, Chem. Commun. 47, 9230, (2011)
  14. - R. Ananthakrishnan, S.Gazi, Catal. Sci. Technol. 2, 1463, (2012)
  15. - L. Shen, S. Cao, J. Wu, J. Zhang, H. Li, N. Liu, X. Qian, Green Chem. 11, 1414, (2009)
  16. - M. M. Aghayan, R. Boukherroub, M. Nemati, M. Rahimifard, Tetrahedron Lett. 53, 2473, (2012)
  17. - A. Debache, R. Boulcina, A. Belfaitah, S. Rhouti, B.Carboni, Synlett 4, 509, (2008)
  18. - S. Thakrar, A. Bavishi, D. Bhavsar, S. Parekh, H. Vala, A. Radadiya, M. Parmar, M. Savant, Synth. Commun. 42, 3269, (2012)
  19. - S. Rostamnia, K. Lamei, Chin. Chem. Lett. 23, 930, (2012)
  20. - A. Kuraitheerthakumaran, S. Pazhamalaian, M. Gopalakrishnan, Chin. Chem. Lett. 22, 1199 (2011)
  21. - N. Koukabi, E. Kolvari, M. A. Zolfigol, A. Khazaei, B. S. Shaghasemi, B. Fasahati, Adv. Synth. Catal., 354, 2001, (2012)
  22. - R. Kumar, N. H. Andhare, A. Shard, A. Richa, K. Sinha. RSC. Adv. 4, 19111, (2014)
  23. - D. Langle, V. Marquardt, E. Heider, B. Vigante, G. Duburs, I. Luntena, D. Flotgen, C. Golz, C. Strohmann, Oliver Koch, D. Schade, Eur. J. Med. Chem. 95, 249, (2015)
  24. - F. Zaera, Chem. Soc. Rev. 42, 2746, (2013)
  25. - N. RaveendranShijuVadim V.Guliants, Appl. Catal., A 356,1, (2009)
  26. - A. H. Lu, E. L. Salabas, F. Schuth, Angew. Chem. Int. Ed. 46, 1222, (2007)
  27. - X. Wu, Y. Guo, L. Wan, C. Hu, J. Phys. Chem. 112, 16824, (2008)
  28. - A. G. Nasibulin, S. Rackauskas, H. Jiang, Nanopart. Res. 2, 373, (2009)
  29. - Z. Guo, D. Zhang, S. Wei, Z. Wang, B. Karki, J. Nanopart. Res. 12, 2415, (2010)
  30. -S. B. Sapkal,K. F. Shelke, B. B. Shingate, M. S. Shingare, Tetrahedron Lett. 50, 1754, (2009)
  31. - M. Abdollahi-Alibeik, S-S. Hoseinikhah, J. Iran Chem. Soc. 13, 1339, (2016)
  32. - R. J. Kalbasi, N. Mosaddegh, Catal. Commun. 12, 1231, (2011)
  33. - E. Vessally, R. Hosseinzadeh‐Khanmiri, E. Ghorbani‐Kalhor, M. Eshaghi, L. Ejlali, Appl. Organomet. Chem. 31, e3729, (2017)
  34. - W. Zhan, Y. Guo, Y. Wang, Y. Guo, X. Liu, Y. Wang, Z. Zhang, G. Lu, J. Phys. Chem. C 113, 7181, (2009)
  35. - N. Mosaddegh, I. Yavari, Chem. Pap. 72, 2013, (2018)
  36. - Y. Duan, D. Zhai, X. Zhang, J. Zheng, C. Li, Catal. Lett. 148, 51, (2018)
  37. - L. Kheirkhah, M. Mamaghani, A. Yahyazadeh, N. O. Mahmoodi, Appl. Organomet. Chem. 32, e4072, (2018)
  38. - M. Ahmadiazar, M. Mamaghani, Curr. Org. Chem. 22, 1326, (2018)
  39. - F. Tavakoli, M. Mamaghani, M. Sheykhan, N. Mohammadipour, M. Rassa, Curr. Org. Synth. 15, 872, (2018)
  40. - M. Mamaghani, M. Sheykhan, M. Sadeghpour, F. Tavakoli, Monatsh. Chem. 149, 1437, (2018)
  41. - P. Jahanshahi, M. Mamaghani, F. Haghbin, R. Hossein Nia, M. Rassa, J. Mol. Struct. 1155, 520, (2018)
  42. - F. Tavakoli, M. Mamaghani, M. Sheykhan, Appl. Organomet. Chem. 33, e5083, (2019)
  43. - P. Jahanshahi, M. Mamaghani, New J. Chem. 43, 8266, (2019)
  44. - F. Ramezanzadeh, M. Mamaghani, H. Fallah-Bagher Shaidaei, M. Sheykhan, Polycycl. Aromat. Comp. DOI: 10.1080/10406638.2019.1705360, (2019)
  45. - E. Saberikhah, M. Mamaghani, N. O. Mahmoodi,; A. Fallah Shojaei, Polycycl. Aromat. Comp. DOI: 10.1080/10406638.2020.1729821, (2020)
  46. - A. Kumar, S. Sharma, V. D. Tripathi, R. A. Maurya, S. P. Srivastava, G. Bhatia, A. K. Tamrakar, A. K. Srivastava, Bioorg. Med. Chem. 18, 4138, (2010)
  47. - C. Witpathomwong, R. Longloilert, S. Wongkasemjit, S. Jitkarnka, Energy Procedia 9, 245, (2011)
  48. - G. M.Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. J. Chem. 7, 335, (2014)
  49. - G.-W. Wang, J.-J.Xia, C.-B. Miao, X.-L. Wu, Bull. Chem. Soc. Jpn. 79, 454, (2006)
  50. - S. Hashemi-Uderji, M. Abdollahi-Alibeik, R. Ranjbar-Karimi, Main Group Met. Chem. 41, 91, (2018)
  51. - K. Ramesh, M. Pasha, Bioorg. Med. Chem. Lett. 24, 3907, (2014)
  52. - M. Saha, A. K. Pal, Tetrahedron Lett. 52, 4872, (2011)
  53. - M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, J. Magn. Magn. Mater. 398, 205, (2016)

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP