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Post‐synthetic modification of IR-MOF‐3 as acidic-basic heterogeneous catalyst for one-pot synthesis of pyrimido[4,5-b]quinolones

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Abstract

In this study, a modified IR-MOF-3 via a multi-step post-synthesis modification, namely IR-MOF-3-ILOAc-Fe(acac)3, was prepared as an ion-pair heterogeneous catalyst for synthesis of pyrimido[4,5-b]quinoline derivatives in the absence of any co-catalyst. Firstly, modified MOF with 4-pyridinecarboxaldehyde (4-PC), followed by 2-chloroethylamine for formation of ionic liquid on the surface (as basic agent) with anion exchange of Cl− to OAc− was prepared. Finally, it was modified with iron(III) acetylacetonate to generate Lewis acid site. The catalyst was characterized by PXRD, FT-IR, FESEM-EDS, TGA and BET techniques. The catalyst has excellent reusability while maintaining continuous activity. A little amount of leaching from the reused catalyst was observed that could be attributed to the loss of the catalyst after each washing process. Kinetic and isotherm of the reaction were also studied.

Graphical abstract

In this study, a modified IR-MOF-3 via a multi-step post-synthesis modification, namely IR-MOF-3-ILOAc-Fe(acac)3, was prepared as ion-pair heterogeneous catalysis for synthesis of pyrimido[4,5-b]quinoline derivatives in the absence of any co-catalyst. Firstly, modified MOF with 4-pyridinecarboxaldehyde (4-PC), followed by 2-chloroethylamine for formation of ionic liquid on the surface (as basic agent) with anion exchange of Cl− to OAc− was prepared. Finally, it was modified with iron(III) acetylacetonate to generate Lewis acid site. The catalyst was characterized by PXRD, FT-IR, FESEM-EDS, TGA and BET techniques. The catalyst has excellent reusability while maintaining continuous activity. A little amount of leaching from the reused catalyst was observed.

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References

  1. J. Guo, Z.D. Tucker, Y. Wang, B.L. Ashfeld, T. Luo, Nat. Commun. 12, 1 (2021)

    Article  Google Scholar 

  2. S.K. Singh, A.W. Savoy, J. Mol. Liq. 297, 112038 (2020)

    Article  CAS  Google Scholar 

  3. K. Chatterjee, A.D. Pathak, A. Lakma, C.S. Sharma, K.K. Sahu, A.K. Singh, Sci. Rep. 10, 1 (2020)

    Article  Google Scholar 

  4. V.C. Ramos, W. Han, X. Zhang, S. Zhang, K.L. Yeung, Curr. Opin. Green Sustain. Chem. 25, 100391 (2020)

    Article  Google Scholar 

  5. V. Campisciano, F. Giacalone, M. Gruttadauria, Chem. Rec. 17, 918 (2017)

    Article  CAS  PubMed  Google Scholar 

  6. C.P. Mehnert, R.A. Cook, N.C. Dispenziere, M. Afeworki, J. Am. Chem. Soc. 124, 12932 (2002)

    Article  CAS  PubMed  Google Scholar 

  7. S. Askari, M.M. Khodaei, M. Jafarzadeh, Res. Chem. Intermed. 47, 2881 (2021)

  8. S. Askari, M. Jafarzadeh, D.B. Christensen, S. Kegnæs, Catal. Lett. 150, 3159 (2020)

    Article  CAS  Google Scholar 

  9. S. Sowmiah, C.I. Cheng, Y.-H. Chu, Curr. Org. Synth. 9, 74 (2012)

    Article  CAS  Google Scholar 

  10. M. O’Keeffe, M.A. Peskov, S.J. Ramsden, O.M. Yaghi, Acc. Chem. Res. 41, 1782 (2008)

    Article  PubMed  Google Scholar 

  11. R.M. Abdelhameed, S. Al Kiey, A.R. Wassel, M. El-Shahat, New J. Chem. 45, 9526 (2021)

    Article  CAS  Google Scholar 

  12. G. Ferey, Chem. Soc. Rev. 37, 191 (2008)

    Article  CAS  PubMed  Google Scholar 

  13. R.M. Abdelhameed, M. Abu-Elghait, M. El-Shahat, J. Photochem. Photobiol. A Chem. 423, 113572 (2022)

    Article  CAS  Google Scholar 

  14. S. Horike, S. Shimomura, S. Kitagawa, Nat. Chem. 1, 695 (2009)

    Article  CAS  PubMed  Google Scholar 

  15. Z. Ju, E.-S.M. El-Sayed, D. Yuan, Dalton Trans. 49, 16617 (2020)

    Article  CAS  PubMed  Google Scholar 

  16. J. Yang, H. Wang, J. Liu, M. Ding, X. **e, X. Yang, Y. Peng, S. Zhou, R. Ouyang, Y. Miao, RSC Adv. 11, 3241 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. B. Panella, M. Hirscher, H. Pütter, U. Müller, Adv. Funct. Mater. 16, 520 (2006)

    Article  CAS  Google Scholar 

  18. J. Liu, P.K. Thallapally, B.P. McGrail, D.R. Brown, J. Liu, Chem. Soc. Rev. 41, 2308 (2012)

    Article  CAS  PubMed  Google Scholar 

  19. B. Panella, M. Hirscher, Adv. Mater. 17, 538 (2005)

    Article  CAS  Google Scholar 

  20. E. Gulcay, I. Erucar, Ind. Eng. Chem. Res. 58, 3225 (2019)

    Article  CAS  Google Scholar 

  21. A. Corma, H. Garcia, F.X. LlabresiXamena, Chem. Rev. 110, 4606 (2010)

    Article  CAS  PubMed  Google Scholar 

  22. A. Henschel, K. Gedrich, R. Kraehnert, S. Kaskel, Chem. Commun. 4192 (2008)

    Article  Google Scholar 

  23. Q. Fang, G. Zhu, M. Xue, J. Sun, G. Tian, G. Wu, S. Qiu, Dalton Trans. 2202 (2004)

    Article  Google Scholar 

  24. G.J. Halder, C.J. Kepert, B. Moubaraki, K.S. Murray, J.D. Cashion, Science 298, 1762 (2002)

    Article  CAS  PubMed  Google Scholar 

  25. L.E. Kreno, K. Leong, O.K. Farha, M. Allendorf, R.P. Van Duyne, J.T. Hupp, Chem. Rev. 112, 1105 (2012)

    Article  CAS  PubMed  Google Scholar 

  26. H.A. Habib, J. Sanchiz, C. Janiak, Dalton Trans. 1734 (2008)

    Article  Google Scholar 

  27. W. Liu, L. Zhang, F. Chen, H. Wang, Q. Wang, K. Liang, Dalton Trans. 49, 3209 (2020)

    Article  CAS  PubMed  Google Scholar 

  28. Y. Zhang, Z. Jiang, J. Song, J. Song, F. Pan, P. Zhang, X. Cao, Ind. Eng. Chem. Res. 58, 16911 (2019)

    Article  CAS  Google Scholar 

  29. R.C. Huxford, J. Della Rocca, W. Lin, Curr. Opin. Chem. Biol. 14, 262 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Y. **e, X. Liu, X. Ma, Y. Duan, Y. Yao, Q. Cai, ACS Appl Mater. Interfaces 10, 13325 (2018)

    Article  CAS  PubMed  Google Scholar 

  31. M. El-Shahat, A.E. Abdelhamid, R.M. Abdelhameed, Carbohydr. Polym. 231, 115742 (2020)

    Article  CAS  PubMed  Google Scholar 

  32. H. Li, M. Eddaoudi, T.L. Groy, O.M. Yaghi, J. Am. Chem. Soc. 120, 8571 (1998)

    Article  CAS  Google Scholar 

  33. H. Li, M. Eddaoudi, M. O’Keeffe, O.M. Yaghi, Nature 402, 276 (1999)

    Article  CAS  Google Scholar 

  34. C. Janiak, J.K. Vieth, New J. Chem. 34, 2366 (2010)

    Article  CAS  Google Scholar 

  35. R. Banerjee, H. Furukawa, D. Britt, C. Knobler, M. O’Keeffe, O.M. Yaghi, J. Am. Chem. Soc. 131, 3875 (2009)

    Article  CAS  PubMed  Google Scholar 

  36. S. Surblé, C. Serre, C. Mellot-Draznicks, F. Millange, G. Férey, Chem. Commun. 284 (2006)

    Article  Google Scholar 

  37. C.-D. Wu, L. Ma, W. Lin, Inorg. Chem. 47, 11446 (2008)

    Article  CAS  PubMed  Google Scholar 

  38. X. Zheng, K. Jiang, L. Zhang, C. Wang, Dalton Trans. 49, 9369 (2020)

    Article  CAS  PubMed  Google Scholar 

  39. S. Rostamnia, H. **n, Appl. Organomet. Chem. 28, 359 (2014)

    Article  CAS  Google Scholar 

  40. M. Wang, L. Guo, D. Cao, Sens. Actuators B 256, 839 (2018)

    Article  CAS  Google Scholar 

  41. V. VenkataSravani, S. Tripathi, B. Sreenivasulu, S. Kumar, S. Maji, C.V.S. Brahmmananda Rao, A. Suresh, N. Sivaraman, RSC Adv. 11, 28126 (2021)

    Article  CAS  Google Scholar 

  42. T. Isobe, Y. Arai, S. Yanagida, S. Matsushita, A. Nakajima, Microporous Mesoporous Mater. 241, 218 (2017)

    Article  CAS  Google Scholar 

  43. Z.-J. Yang, Q.-T. Gong, Y. Wang, Y. Yu, Y.-H. Liu, N. Wang, X.-Q. Yu, Mol. Catal. 491, 110983 (2020)

    Article  CAS  Google Scholar 

  44. F. Kamali, F. Shirini, Appl. Organomet. Chem. 32, e3972 (2018)

    Article  Google Scholar 

  45. Y. Gu, Green Chem. 14, 2091 (2012)

    Article  CAS  Google Scholar 

  46. R. Kordnezhadian, M. Shekouhy, A. Khalafi-Nezhad, New J. Chem. 43, 18559 (2019)

    Article  CAS  Google Scholar 

  47. M.H. Sayahi, M. Gorjizadeh, M. Meheiseni, S. Sayyahi, Z. Naturforschung 75b, 269 (2020)

    Article  Google Scholar 

  48. R. Khanivar, A.Z. Zare, Naturforschung 73b, 635 (2018)

    Article  Google Scholar 

  49. J. Elguero, in Comprehensive Heterocyclic Chemistry, vol. 3, ed. by A.R. Katritzky, C.W. Rees, E.F. Scriven (Pergamon Press, Oxford, 1996), p. 1

    Google Scholar 

  50. M. Kidwai, N. Negi, Monatsh. Chem. 128, 85 (1997)

    Article  CAS  Google Scholar 

  51. D.R. Huron, M.E. Gorre, A.J. Kraker, L. Charles, M.M. Moasser, Clin. Cancer Res. 9, 1267 (2003)

    CAS  PubMed  Google Scholar 

  52. L.V.G. Nargund, V.V. Badiger, S.M. Yarnal, J. Pharm. Sci. 81, 365 (1992)

    Article  CAS  PubMed  Google Scholar 

  53. A.A. El-Sayed, M. El-Shahat, S.T. Rabie, E.M. Flefel, D.N. Abd-Elshafy, Int. J. Pharm. 5, 69 (2015)

    Google Scholar 

  54. Y. **a, Z.Y. Yang, P. **a, K.F. Bastow, Y. Tachibana, S.C. Kuo, E. Hamel, T. Hackl, K.H. Lee, J. Med. Chem. 41, 1155 (1998)

    Article  CAS  PubMed  Google Scholar 

  55. G.J. Atwell, B.C. Baguley, W.A. Denny, J. Med. Chem. 32, 396 (1989)

    Article  CAS  PubMed  Google Scholar 

  56. V. Alagarsamy, Pharmazie 59, 753 (2004)

    CAS  PubMed  Google Scholar 

  57. A.A. Joshi, S.S. Narkhede, C.L. Viswanathan, Bioorg. Med. Chem. Lett. 15, 73 (2005)

    Article  CAS  PubMed  Google Scholar 

  58. K. Tabatabaeian, A.F. Shojaei, F. Shirini, S.Z. Hejazi, M. Rassa, Chin. Chem. Lett. 25, 308 (2014)

    Article  CAS  Google Scholar 

  59. T.H. Althuis, P.F. Moore, H.J. Hess, J. Med. Chem. 22, 44 (1979)

    Article  CAS  PubMed  Google Scholar 

  60. A.B.A. El-Gazzar, H.N. Hafez, G.A.M. Nawwar, Eur. J. Med. Chem. 44, 1427 (2009)

    Article  CAS  PubMed  Google Scholar 

  61. E. Rajanarendar, M. Nagi Reddy, S. Rama Krishna, K. Rama Murthy, Y.N. Reddy, M.V. Rajam, Eur. J. Med. Chem. 55, 273 (2012)

    Article  CAS  PubMed  Google Scholar 

  62. M.M. Ghorab, F.A. Ragab, H.I. Heiba, R.K. Arafa, E.M. El-Hossary, Eur. J. Med. Chem. 45, 3677 (2010)

    Article  CAS  PubMed  Google Scholar 

  63. S.I. Alqasoumi, A.M. Al-Taweel, A.M. Alafeefy, E. Noaman, M.M. Ghorab, Eur. J. Med. Chem. 45, 738 (2010)

    Article  CAS  PubMed  Google Scholar 

  64. L. Edjlali, R. HosseinzdehKhanamiri, J. Abolhasani, Monatsh. Chem. 146, 1339 (2015)

    Article  CAS  Google Scholar 

  65. F. Shirini, M. Safarpoor, N. Langarudi, N. Daneshvar, M. Mashhadinezhad, N. Nabinia, J. Mol. Liq. 243, 302 (2017)

    Article  CAS  Google Scholar 

  66. A. Zare, M. Dianat, M.M. Eskandari, New J. Chem. 44, 4736 (2020)

    Article  CAS  Google Scholar 

  67. K. Mohammadi, F. Shirini, A. Yahyazadeh, RSC Adv. 5, 23586 (2015)

    Article  CAS  Google Scholar 

  68. F. Shirini, M. Safarpoor, N. Langarudi, N. Daneshvar, N. Jamasbi, M. Irankhah-Khanghah, J. Mol. Struct. 1161, 366 (2018)

    Article  CAS  Google Scholar 

  69. A. Zare, N. Lotfifar, M. Dianat, J. Mol. Struct. 1211, 128030 (2020)

    Article  CAS  Google Scholar 

  70. A. Zare, M. Dianat, Z. Naturforschung B 76, 85 (2021)

    Article  Google Scholar 

  71. Y.-J. Kim, D.-W. Park, J. Nanosci. Nanotechnol. 13, 2307 (2013)

    Article  CAS  PubMed  Google Scholar 

  72. Z. Wu, X. Huang, H. Zheng, P. Wang, G. Hai, W. Dong, G. Wang, Appl. Catal. B 224, 479 (2018)

    Article  CAS  Google Scholar 

  73. M.M. Mostafavi, F. Movahedi, Eur. J. Inorg. Chem. 2019, 787 (2019)

    Article  CAS  Google Scholar 

  74. G. Gao, J.-Q. Di, H.-Y. Zhang, L.-P. Mo, Z.-H. Zhang, J. Catal. 387, 39 (2020)

    Article  CAS  Google Scholar 

  75. A. Kumar, A.R. Chowdhuri, A. Kumari, S.K. Sahu, Mater. Sci. Eng. C 92, 913 (2018)

    Article  CAS  Google Scholar 

  76. M. Cai, L. Qin, L. Pang, B. Ma, J. Bai, J. Liu, X. Dong, X. Yin, J. Ni, New J. Chem. 44, 17693 (2020)

    Article  Google Scholar 

  77. A. Nuri, N. Vucetic, J.-H. Smått, Y. Mansoori, J.-P. Mikkola, D.Y. Murzin, Catal. Lett. 149, 1941 (2019)

    Article  CAS  Google Scholar 

  78. M. Thommes, K. Kaneko, A.V. Neimark, J.P. Olivier, F. Rodriguez-Reinoso, J. Rouquerol, K.S. Sing, Pure Appl. Chem. 87, 1051 (2015)

    Article  CAS  Google Scholar 

  79. F. Osanlou, F. Nemati, S. Sabaqian, Res. Chem. Intermed. 43, 2159 (2017)

    Article  CAS  Google Scholar 

  80. Ü. Kökçam-Demir, A. Goldman, L. Esrafili, M. Gharib, A. Morsali, O. Weingart, C. Janiak, Chem. Soc. Rev. 49, 2751 (2020)

    Article  PubMed  Google Scholar 

  81. H. Chen, L. Fan, X. Zhang, ACS Appl Mater. Interface 12, 54884 (2020)

    Article  CAS  Google Scholar 

  82. A. Gholami, M. Mokhtary, M. Nikpassand, Appl. Organomet. Chem. 34, e6007 (2020)

    Article  CAS  Google Scholar 

  83. S. Abdolmohammadi, S. Balalaie, M. Barari, F. Rominger, Comb. Chem. High Throughput Screen. 16, 150 (2013)

    CAS  PubMed  Google Scholar 

  84. D. Verma, V. Sharma, G.S. Okram, S. Jain, Green Chem. 19, 5885 (2017)

    Article  CAS  Google Scholar 

  85. X. Yao, X. Wang, Y. Han, P. Yan, Y. Li, G. Li, CrystEngComm 20, 3335 (2018)

    Article  CAS  Google Scholar 

  86. Z.A. Piskulich, O.O. Mesele, W.H. Thompson, J. Phys. Chem. A 123, 7185 (2019)

    Article  CAS  PubMed  Google Scholar 

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  1. Department of Organic Chemistry, Razi University, 67149-67346, Kermanshah, Iran

    Zahra Karami & Mohammad Mehdi Khodaei

  2. Nanoscience and Nanotechnology Research Center (NNRC), Razi University, 67149-67346, Kermanshah, Iran

    Mohammad Mehdi Khodaei

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Karami, Z., Khodaei, M.M. Post‐synthetic modification of IR-MOF‐3 as acidic-basic heterogeneous catalyst for one-pot synthesis of pyrimido[4,5-b]quinolones. Res Chem Intermed 48, 1773–1792 (2022). https://doi.org/10.1007/s11164-022-04678-w

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