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Design and exploration of caffeine-based Brönsted acidic ionic liquid (CaffBAIL) for the synthesis of DHPMs, xanthenediones, and acridinediones

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Abstract

A novel caffeine-based acidic ionic liquid was synthesized, characterized, and utilized as an efficient and green catalyst for synthesizing DHPMs, xanthenediones, and acridinediones under solvent-free conditions. The prepared IL showed notable catalytic activity in organic reactions under solvent-free conditions with good reusability of four runs. The advantage of the present protocol is underlined by the originality of the prepared ionic liquid, absence of toxic solvents, high yields of products, and short reaction times.

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References

  1. M.A. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)

    Article  CAS  PubMed  Google Scholar 

  2. N. Isambert, M.D. Duque, J.-C. Plaquevent, Y. Genisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347 (2011)

    Article  CAS  PubMed  Google Scholar 

  3. M. Salami, A. Ezabadi, Res. Chem. Intermed. 45, 3673 (2019)

    Article  CAS  Google Scholar 

  4. S.E.S. Sorkhi, M.M. Hashemi, A. Ezabadi, Res. Chem. Intermed. 46, 2229 (2020)

    Article  CAS  Google Scholar 

  5. Z.A. Piralghar, M.M. Hashemi, A. Ezabadi, Polycycl. Aromat. Compd. 40, 1510 (2019)

    Article  CAS  Google Scholar 

  6. R. Padmaja, K. Chanda, Res. Chem. Intermed. 46, 1307 (2020)

    Article  CAS  Google Scholar 

  7. M. Zabihzadeh, F. Shirini, H. Tajik, N. Daneshvar, Polycyclic Aromat. Compd. 41, 1972 (2021)

  8. F. Rezaei, M.A. Amrollahi, R. Khalifeh, ChemSelect 5, 1760 (2020)

    CAS  Google Scholar 

  9. R. Larsson, Stud. Surf. Sci. Catal. 79, 3 (1981)

    Google Scholar 

  10. F. Arian, M. Keshavarz, H. Sanaeishoar, N. Hasanzadeh, J. Mol. Struct. 1229, 129599 (2021)

    Article  CAS  Google Scholar 

  11. S. Rostamizadeh, M. Rezgi, N. Shadjou, M. Hasanzadeh, J. Chin. Chem. Soc. 60, 11 (2013)

  12. M. Alvala, S. Bhatnagar, A. Ravi, V.U. Jeankumar, T.H. Manjashetty, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 22, 3256 (2012)

    Article  CAS  PubMed  Google Scholar 

  13. M.M. Patel, M.D. Mali, S.K. Patel, Bioorg. Med Chem. Lett. 20, 6324 (2010)

    Article  CAS  PubMed  Google Scholar 

  14. C.H. Cheon, H. Yamamoto, Chem. Commun. 47, 3043 (2011)

    Article  CAS  Google Scholar 

  15. J. Li, C. Chen, Y. Hu, ChemistrySelect, 5, 14578 (2020)

  16. Z. Qi, Z. Huang, H. Wang, L. Li, C. Ye, T. Qiu, Chem. Eng. Sci. 225, 115818 (2020)

    Article  CAS  Google Scholar 

  17. S. El Sayed, A. Bordet, C. Weidenthaler, W. Hetaba, K.L. Luska, W. Leitner, ACS Catal. 10, 2124 (2020)

    Article  CAS  Google Scholar 

  18. N. Yao, C. Chen, Y.L. Hu, J. Environ. Chem. Eng. 8, 103953 (2020)

    Article  CAS  Google Scholar 

  19. L. Hao, L. Sun, T. Su, D. Hao, W. Liao, C. Deng, W. Ren, Y. Zhang, H. Lü, Chem. Eng. J. 358, 419 (2019)

    Article  CAS  Google Scholar 

  20. J.C. Menéndez, Synthesis 2006, 2624 (2006)

    Article  Google Scholar 

  21. C.O. Kappe, Acc. Chem. Res. 33, 879 (2000)

    Article  CAS  PubMed  Google Scholar 

  22. H. Nagarajaiah, A. Mukhopadhyay, J.N. Moorthy, Tetrahedron Lett. 57, 5135 (2016)

    Article  CAS  Google Scholar 

  23. S.R. Patil, A.S. Choudhary, V.S. Patil, N. Sekar, Fibers Polym. 16, 2349 (2015)

    Article  CAS  Google Scholar 

  24. A.C. Boukis, A. Llevot, M.A. Meier, Macromol. Rapid Commun. 37, 643 (2016)

    Article  CAS  PubMed  Google Scholar 

  25. Y. Zhao, Y. Yu, Y. Zhang, X. Wang, B. Yang, Y. Zhang, Q. Zhang, C. Fu, Y. Wei, L. Tao, Polym. Chem. 6, 4940 (2015)

    Article  CAS  Google Scholar 

  26. S.F. Taheri Hatkehlouei, B. Mirza, S. Soleimani-Amiri, Polycycl. Aromat. Compd., 1 (2020)

  27. B.M. Patil, S.K. Shinde, A.A. Jagdale, S.D. Jadhav, S.S. Patil, Res. Chem. Intermed. 47, 4369 (2021)

    Article  CAS  Google Scholar 

  28. M.-S. Mashhoori, R. Sandaroos, A.Z. Moghaddam, Res. Chem. Intermed. 46, 4939 (2020)

    Article  CAS  Google Scholar 

  29. H. Wu, X.-M. Chen, Y. Wan, H.-Q. Xin, H.-H. Xu, C.-H. Yue, L.-L. Pang, R. Ma, Synth. Commun. 39, 3762 (2009)

    Article  CAS  Google Scholar 

  30. O. Evangelinou, A. Hatzidimitriou, E. Velali, A. Pantazaki, N. Voulgarakis, P. Aslanidis, Polyhedron 72, 122 (2014)

    Article  CAS  Google Scholar 

  31. L. Yunnikova, V.Y. Gorokhov, T. Makhova, G. Aleksandrova, Pharm. Chem. J. 47, 139 (2013)

    Article  CAS  Google Scholar 

  32. S.-L. Niu, Z.-L. Li, F. Ji, G.-Y. Liu, N. Zhao, X.-Q. Liu, Y.-K. Jing, H.-M. Hua, Phytochemistry 77, 280 (2012)

    Article  CAS  PubMed  Google Scholar 

  33. J.P. Poupelin, G. Saint‐Ruf, O. Foussard‐Blanpin, G. Marcisse, G. Uchida‐Ernouf, R. Lacroix, Chem. Inform. 9, 25 (1978)

  34. G.L.N. Djoufack, K.M. Valant-Vetschera, J. Schinnerl, L. Brecker, E. Lorbeer, W. Robien, Nat. Prod. Commun. 5, 1055 (2010)

    CAS  PubMed  Google Scholar 

  35. T.F. Diniz, A.C. Pereira, L.S. Capettini, M.H. Santos, T.J. Nagem, V.S. Lemos, S.F. Cortes, Planta Med. 79, 1495 (2013)

    Article  CAS  PubMed  Google Scholar 

  36. W. Maneerat, S. Laphookhieo, S. Koysomboon, K. Chantrapromma, Phytomedicine 15, 1130 (2008)

    Article  CAS  PubMed  Google Scholar 

  37. N. Patel, U. Patel, A. Dadhania, Res. Chem. Intermed. 47, 2189 (2021)

    Article  CAS  Google Scholar 

  38. Z. Zhou, X. Deng, J. Mol. Catal. A Chem. 367, 99 (2013)

    Article  CAS  Google Scholar 

  39. B. Maleki, A. Davoodi, M.V. Azghandi, M. Baghayeri, E. Akbarzadeh, H. Veisi, S.S. Ashrafi, M. Raei, New J. Chem. 40, 1278 (2016)

    Article  CAS  Google Scholar 

  40. P.J. Das, J. Das, RSC Adv. 5, 11745 (2015)

    Article  CAS  Google Scholar 

  41. D. Thirumalai, S. Gajalakshmi, Res. Chem. Intermed. 46, 2657 (2020)

    Article  CAS  Google Scholar 

  42. A. Olyaei, A. Adl, E. Vessally, Res. Chem. Intermed. 47, 2207 (2021)

    Article  CAS  Google Scholar 

  43. N. Azizi, F. Abbasi, M. Abdoli-Senejani, ChemSelect 3, 3797 (2018)

    CAS  Google Scholar 

  44. A. Amoozadeh, S.F. Hosseininya, S. Rahmani, Res. Chem. Intermed. 44, 991 (2018)

    Article  CAS  Google Scholar 

  45. F. Abbasi, N. Azizi, M. Abdoli-Senejani, J. Iran. Chem. Soc. 14, 2097 (2017)

    Article  CAS  Google Scholar 

  46. N. Hazeri, A. Masoumnia, M.T. Mghsoodlou, S. Salahi, M. Kangani, S. Kianpour, S. Kiaee, J. Abonajmi, Res. Chem. Intermed. 41, 4123 (2015)

    Article  CAS  Google Scholar 

  47. F. Rajabi, M. Pinilla-de Dios, M. Abdollahi, R. Luque, Catal. Commun. 120, 95 (2019)

    Article  CAS  Google Scholar 

  48. M. Schramm, G. Thomas, R. Towart, G. Franckowiak, Nature 303, 535 (1983)

    Article  CAS  PubMed  Google Scholar 

  49. K. Ramesh, M. Pasha, Bioorg. Med. Chem. Lett. 24, 3907 (2014)

    Article  CAS  PubMed  Google Scholar 

  50. N. Edraki, A.R. Mehdipour, M. Khoshneviszadeh, R. Miri, Drug Discov. Today 14, 1058 (2009)

    Article  CAS  PubMed  Google Scholar 

  51. S. Chehab, Y. Merroun, T. Ghailane, R. Ghailane, S. Boukhris, M. Akhazzane, A. Kerbal, A. Souizi, Russ. J. Org. Chem. 55, 1380 (2019)

    Article  CAS  Google Scholar 

  52. B. Sardar, R. Jamatia, D. Pal, D. Srimani, Asian J. Org. Chem. 10, 2195 (2021)

    Article  CAS  Google Scholar 

  53. A. Tambe, A. Gadhave, A. Pathare, G. Shirole, Sustain. Chem. Pharm. 22, 100485 (2021)

    Article  CAS  Google Scholar 

  54. S.R. Mousavi, H. Rashidi Nodeh, A. Foroumadi, Polycycl. Aromat. Compd. 41, 746 (2021)

    Article  CAS  Google Scholar 

  55. A.Y.E. Abadi, M.-T. Maghsoodlou, R. Heydari, R. Mohebat, Res. Chem. Intermed. 42, 1227 (2016)

    Article  CAS  Google Scholar 

  56. F. Mohamadpour, M. Lashkari, J. Serb. Chem. Soc. 83, 673 (2018)

    Article  CAS  Google Scholar 

  57. M. Salami, A. Ezabadi, Res. Chem. Intermed. 46, 4611 (2020)

    Article  CAS  Google Scholar 

  58. H. Sahebi, E. Konoz, A. Ezabadi, New J. Chem. 43, 13554 (2019)

    Article  CAS  Google Scholar 

  59. Z. Abdi Piralghar, M.M. Hashemi, A. Ezabadi, Polycyclic Aromat. Compd. 40, 1510 (2019)

  60. Z. Ehsani-Nasab, A. Ezabadi, Comb. Chem. High Throughput Screen. 21, 602 (2018)

    Article  CAS  PubMed  Google Scholar 

  61. Z.A. Piralghar, M.M. Hashemi, A. Ezabadi, Comb. Chem. High Throughput Screen 21, 526 (2018)

    Article  CAS  PubMed  Google Scholar 

  62. A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 186, 63 (2013)

    Article  CAS  Google Scholar 

  63. Z. Karimi-Jaberi, M.S. Moaddeli, ISRN Org. Chem. 2012, 1 (2012)

    Article  CAS  Google Scholar 

  64. K.M. Hua, P.H. Tran, T.N. Le, ARKIVOC 6, 406 (2019)

    Google Scholar 

  65. S. Gore, S. Baskaran, B. Koenig, Green Chem. 13, 1009 (2011)

    Article  CAS  Google Scholar 

  66. S. Sabaqian, F. Nemati, H.T. Nahzomi, M.M. Heravi, Carbohydr. Polym. 177, 165 (2017)

    Article  CAS  PubMed  Google Scholar 

  67. M. Salami, A. Ezabadi, Polycycl. Aromat. Compd., 1 (2020)

  68. Á. Magyar, Z. Hell, Catal. Lett. 149, 2528 (2019)

    Article  CAS  Google Scholar 

  69. N. Martín, M. Quinteiro, C. Seoane, J.L. Soto, A. Mora, M. Suárez, E. Ochoa, A. Morales, J.R.D. Bosque, J. Heterocycl. Chem. 32, 235 (1995)

    Article  Google Scholar 

  70. S. Balalaie, F. Chadegani, F. Darviche, H.R. Bijanzadeh, Chin. J. Chem. 27, 1953 (2009)

    Article  CAS  Google Scholar 

  71. R. Kong, S.-B. Han, J.-Y. Wei, X.-C. Peng, Z.-B. Xie, S.-S. Gong, Q. Sun, Molecules 24, 364 (2019)

    Article  PubMed Central  CAS  Google Scholar 

  72. B. Mohammadi, F.K. Behbahani, G.B. Marandi, B. Mirza, Phosphorus Sulfur Silicon Relat. Elem. 196, 54 (2020)

    Article  CAS  Google Scholar 

  73. D. Elhamifar, A. Shabani, Chem. Eur. J 20, 3212 (2014)

    Article  CAS  PubMed  Google Scholar 

  74. A. Ilangovan, S. Malayappasamy, S. Muralidharan, S. Maruthamuthu, Chem. Cent. J. 5, 1 (2011)

    Article  CAS  Google Scholar 

  75. S. Kamalifar, H. Kiyani, Polycycl. Aromat. Compd., 1 (2021)

  76. D. Aute, A. Kshirsagar, B. Uphade, A. Gadhave, J. Heterocycl. Chem. 57, 3691 (2020)

    Article  CAS  Google Scholar 

  77. F. Rajabi, M. Abdollahi, E.S. Diarjani, M.G. Osmolowsky, O.M. Osmolovskaya, P. Gómez-López, A.R. Puente-Santiago, R. Luque, Materials 12, 2386 (2019)

    Article  CAS  PubMed Central  Google Scholar 

  78. G.M. Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. J. Chem. 7, 335 (2014)

    Article  CAS  Google Scholar 

  79. A.K. Dutta, P. Gogoi, R. Borah, RSC Adv. 4, 41287 (2014)

    Article  CAS  Google Scholar 

  80. A. Abdelghany, A. Menazea, M.A. Abd-El-Maksoud, T.K. Khatab, Appl. Organomet. Chem. 34, e5250 (2020)

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, Central Tehran Branch, Islamic Azad University Tehran, Tehran, Iran

    Elaheh Hataminejad & Ali Ezabadi

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Hataminejad, E., Ezabadi, A. Design and exploration of caffeine-based Brönsted acidic ionic liquid (CaffBAIL) for the synthesis of DHPMs, xanthenediones, and acridinediones. Res Chem Intermed 48, 2535–2556 (2022). https://doi.org/10.1007/s11164-022-04724-7

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