‎[Cu(3-hydroxy-2-naphtoate)2].4H2O: A Novel Reusable Heterogeneous ‎Catalyst for Synthesis of Polyhydroquinoline and 2,3-‎Dihydroquinazoline- 4(1H)-one Derivatives

Document Type : Research Paper


1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

2 Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, Iran



Herein, the catalytic performance of [Cu(3-hydroxy-2-naphtoate)2].4H2O complex has been examinated in synthesis of polyhydroquinoline and 2,3-dihydroquinazoline-4(1H)-one derivatives. The catalytic reactions have been carried out in solvent-free conditions. The obtained results have showed that the complex has high catalytic activity, so that the desired products were obtained in good to high yields. Moreover, the investigated catalyst was found to be reusable, which could be achieved after 3rd run with a considerable catalytic activity.

Graphical Abstract

‎[Cu(3-hydroxy-2-naphtoate)2].4H2O: A Novel Reusable Heterogeneous ‎Catalyst for Synthesis of Polyhydroquinoline and 2,3-‎Dihydroquinazoline- 4(1H)-one Derivatives


  1. F. A. Filho, B. C. Lemos, A. S. de Souza, S. Pinheiro, S. J. Greco, Tetrahedron, 2017, 73, 6977-7004.
  2. M. A. Pinto, O. Adeoye, S. S. Thomasi, A. P. Francisco, H. Cabral-Marques, J. Mol. Struct., 2021, 1237, 130391.
  3. Deng, J. Liang, G. Yang, Q. Huang, J. Dou, J. Chen, Y. Wen, M. Liu, X. Zhang, Y. Wei, J. Environ. Chem. Eng., 2021, 9, 104872.
  4. V. Machado, J. R. N. dos Santos, M. A. P. Januario, A. G. Corrêa, Ultrason. Sonochem., 2021, 78, 105704.
  5. Tandi, S. Sundriyal, J. Indian Chem. Soc., 2021, 98, 100106.
  6. Maleki, O. Reiser, E. Esmaeilnezhad, H. J. Choi, Polyhedron, 2019, 162, 129-141.
  7. Kajihara, S. Harada, J. Ueda, T. Nemoto, Tetrahedron Lett., 2018, 59, 1906-1908.
  8. C. Karad, V. B. Purohit, D. K. Raval, P. N. Kalaria, J. R. Avalani, P. Thakor, V. R. Thakkar, RSC Adv., 2015, 5, 16000-16009.
  9. M. Chandrika, T. Yakaiah, A. R. R. Rao, B. Narsaiah, N. C. Reddy, V. Sridhar, J. V. Rao, Eur. J. Med. Chem. 2008, 43, 846-852.
  10. N. Kalaria, S. P. Satasia, D. K. Raval, European Journal of Medicinal Chemistry, 2014, 78, 207-216.
  11. -S. Li, X. -Y. Liu, D. -S. Zhao, Y. -X. Liao, L. -H. Zhang, F. -Z. Zhang, G. -P. Song, Z. -N. Cui, Bioorg. Med. Chem. Lett. 2018, 28, 3271-3275.
  12. Zheng, Q. Dai, Z. Yuan, T. Fan, C. Zhang, Z. Liu, B. Chu, Q. Sun, Y. Chen, Y. Jiang, Bioorg. Med. Chem., 2022, 53, 116524.
  13. Li, Y. Ouyang, H. Wu, P. Wang, Y. Huang, X. Li, H. Chen, Y. Sun, X. Hu, X. Wang, G. Li, Y. Lu, C. Li, X. Lu, J. Pang, T. Nie, X. Sang, L. Dong, W. Dong, J. Jiang, I. C. Paterson, X. Yang, W. Hong, H. Wang, X. You, Eur. J. Med. Chem., 2021, DOI: https://doi.org/10.1016/j.ejmech.2021.113979, 113979.
  14. K. Parhi, Y. Zhang, K. W. Saionz, P. Pradhan, M. Kaul, K. Trivedi, D. S. Pilch, E. J. LaVoie, Bioorg. Med. Chem. Lett., 2013, 23, 4968-4974.
  15. Nikoorazm, Z. Erfani, Chem. Phys. Lett., 2019, 737, 136784.
  16. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, H. Veisi, Solid State Sci., 2019, 91, 96-107.
  17. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, Chin. J. Catal., 2013, 34, 1173-1178.
  18. Chen, W. Su, H. Wu, M. Liu, C. Jin, Green Chem., 2007, 9, 972-975.
  19. Wu, X. Du, J. Ma, Y. Zhang, Q. Shi, L. Luo, B. Song, S. Yang, D. Hu, Green Chem., 2014, 16, 3210-3217.
  20. Hajjami, B. Tahmasbi, Rsc Adv., 2015, 5, 59194-59203.
  21. Khashi, A. Davoodnia, V. P. R. Lingam, Res. Chem. Intermed., 2015, 41, 5731-5742.
  22. Khashi, S. A. Beyramabadi, A. Davoodnia, Z. Ettehadi, J. Mol. Struct., 2017, 1134, 789-796.
  23. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, R. Moloudi, H. A. Zamani, Monatsh. Chem., 2013, 144, 677-680.
  24. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, N. Tavakoli-Hoseini, Chin. Chem. Lett., 2010, 21, 1-4.
  25. Jafari-Moghaddam, S. A. Beyramabadi, M. Khashi, A. Morsali, J. Mol. Struct., 2018, 1153, 149-156.
  26. Davoodnia, M. Bakavoli, R. Moloudi, N. Tavakoli-Hoseini, M. Khashi, Monatsh. Chem., 2010, 141, 867-870.
  27. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, Chin. J. Catal., 2014, 35, 1054-1058.
  28. Khashi, S. Allameh, S. A. Beyramabadi, A. Morsali, E. Dastmalchian, A. Gharib, Iran. J. Chem. Chem. Eng., 2017, 36, 45-52.
  29. A. A. Khoshdast, S. A. Beyramabadi, M. Khashi, A. Morsali, M. Pordel, Bul. Chem. Commun., 2017, 49, 35-41.
  30. Ko, M. Sastry, C. Lin, C. -F. Yao, Tetrahedron Lett., 2005, 46, 5771-5774.
  31. L. Donelson, R. A. Gibbs, S. K. De, J. Mol. Catal. A: Chem., 2006, 256, 309-311.
  32. B. Sapkal, K. F. Shelke, B. B. Shingate, M. S. Shingare, Tetrahedron Lett., 2009, 50, 1754-1756.
  33. S. Reddy, M. Raghu, Chin. Chem. Lett., 2008, 19, 775-779.
  34. -M. Wang, J. Sheng, L. Zhang, J. -W. Han, Z. -Y. Fan, H. Tian, C. -T. Qian, Tetrahedron, 2005, 61, 1539-1543.
  35. Yassaghi, A. Davoodnia, S. Allameh, A. Zare-Bidaki, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 2012, 33, 2724-2730.
  36. Lei, M. Zhang, G. Leng, C. Ding, Y. Ni, Microporous Mesoporous Mater. 2020, 299, 110110.
  37. Song, J. Wang, L. Yang, H. Pan, B. Zheng, Inorg. Chem. Commun., 2020, 121, 108197.
  38. Li, Y. Zhi, P. Shao, H. Xia, G. Li, X. Feng, X. Chen, Z. Shi, X. Liu, Appl. Catal., B, 2019, 245, 334-342.
  39. Bakherad, R. Doosti, M. Mirzaee, K. Jadidi, Iran. J. Catal., 2017, 7, 277.
Volume 6, Issue 1
Spring and Summer; Special Issue: In Memory of Prof. Mehdi Rashidi
Pages 26-30
  • Receive Date: 09 May 2021
  • Revise Date: 21 December 2021
  • Accept Date: 19 January 2022
  • First Publish Date: 20 February 2022