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Introduction of a novel dicationic Brönsted acidic ionic liquid based on pyrazine and its application in the synthesis of xanthenediones and 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions

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Abstract

A novel dicationic Brönsted acidic ionic liquid based on pyrazine has been prepared and characterized by FTIR, 1H NMR, 13C NMR, MS, thermal gravimetric and differential thermal gravimetric analysis and also Hammett acidity function. The prepared dicationic ionic liquid is found to be an efficient and reusable catalyst for the synthesis of xanthenediones and 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. The merits of the developed procedure include novelty in terms of the ionic liquid, easy preparation of the ionic liquid, easy workup, reusability of the catalyst, high yield, short reaction time and absence of toxic organic solvent.

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References

  1. R.L. Vekariya, J. Mol. Liq. 227, 44 (2017)

    Article  CAS  Google Scholar 

  2. M. Parveen, S. Azaz, A.M. Malla, F. Ahmad, P.S.P. da Silva, M.R. Silva, New J. Chem. 39, 469 (2015)

    Article  CAS  Google Scholar 

  3. M. Talebi, R.A. Patil, D.W. Armstrong, J. Mol. Liq. 256, 247 (2018)

    Article  CAS  Google Scholar 

  4. S. Steudte, S. Bemowsky, M. Mahrova, U. Bottin-Weber, E. Tojo-Suarez, P. Stepnowski, S. Stolte, RSC Adv. 4, 5198 (2014)

    Article  CAS  Google Scholar 

  5. A.N. Masri, M.A. Mutalib, N.F. Aminuddin, J.-M. Leveque, Sep. Purif. Technol. 196, 106 (2018)

    Article  CAS  Google Scholar 

  6. N. Daneshvar, M. Nasiri, M. Shirzad, M.S.N. Langarudi, F. Shirini, H. Tajik, New J. Chem. 42, 9744 (2018)

    Article  CAS  Google Scholar 

  7. J. Chen, L. Yang, W. Zhou, L. Zhu, Y. Zhou, Y. Xiang, D. Xia, Energy Fuels 32, 5518 (2018)

    Article  CAS  Google Scholar 

  8. A. Dhar, N.S. Kumar, M. Asif, R.L. Vekariya, New J. Chem. 42, 6990 (2018)

    Article  CAS  Google Scholar 

  9. T. Hideo, Chem. Abstr. 95, 80922b (1981)

    Google Scholar 

  10. J.P. Poupelin, G. Saintruf, R. Lacroix, G. Narcisse, O. Foussardblanpin, G. Uchidaernouf, Eur. J. Med. Chem. 13, 381 (1978)

    CAS  Google Scholar 

  11. R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G. Thomas, Chem. Abstr. 126, p212377y (1997)

    Google Scholar 

  12. G. Saintruf, J.P. Poupelin, Naturwissenschaften 62, 584 (1975)

    Article  CAS  Google Scholar 

  13. R.-M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, Acta Biochim. Pol. 45, 833 (1998)

    Article  CAS  PubMed  Google Scholar 

  14. V.R. Narayana, Z. Pudukulathan, R. Varala, Organ. Commun. 6, 110 (2013)

    CAS  Google Scholar 

  15. P. Iniyavan, S. Sarveswari, V. Vijayakumar, Res. Chem. Intermed. 41, 7413 (2015)

    Article  CAS  Google Scholar 

  16. M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigm. 76, 836 (2008)

    Article  CAS  Google Scholar 

  17. A. Rahmati, Chin. Chem. Lett. 21, 761 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. G.R. Chaudhary, P. Bansal, N. Kaur, S. Mehta, RSC Adv. 4, 49462 (2014)

    Article  CAS  Google Scholar 

  20. 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 

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

    Article  CAS  Google Scholar 

  22. A. Ilangovan, S. Malayappasamy, S. Muralidharan, S. Maruthamuthu, Chem. Cent. J. 5, 81 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. H. Ulusal, G. Fındıkkıran, O. Demirkol, D. Akbaşlar, E.S. Giray, J. Supercrit. Fluid. 105, 146 (2015)

    Article  CAS  Google Scholar 

  24. A.N. Dadhania, V.K. Patel, D.K. Raval, J. Saudi Chem. Soc. 21, S163 (2017)

    Article  CAS  Google Scholar 

  25. K. Gong, H. Wang, S. Wang, Y. Wang, J. Chen, Chin. J. Catal. 36, 1249 (2015)

    Article  CAS  Google Scholar 

  26. A. Thakur, A. Sharma, A. Sharma, Synth. Commun. 46, 1766 (2016)

    Article  CAS  Google Scholar 

  27. A. Rajini, C. Suman, A. Ajay Kumar, S. Suresh, N. Venkatathri, Synth. Commun. 46, 1671 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. Z.-H. Zhang, Y.-H. Liu, Catal. Commun. 9, 1715 (2008)

    Article  CAS  Google Scholar 

  30. H.Y. Lue, J.J. Li, Z.H. Zhang, Appl. Organomet. Chem. 23, 165 (2009)

    Article  CAS  Google Scholar 

  31. M.A. Ghasemzadeh, J. Safaei-Ghomi, S. Zahedi, J. Serb. Chem. Soc. 78, 769 (2013)

    Article  CAS  Google Scholar 

  32. G.K. Verma, K. Raghuvanshi, R.K. Verma, P. Dwivedi, M. Singh, Tetrahedron 67, 3698 (2011)

    Article  CAS  Google Scholar 

  33. D. Fang, J.M. Yang, Z.L. Liu, J. Heterocycl. Chem. 48, 468 (2011)

    Article  CAS  Google Scholar 

  34. F. Shirini, M.S.N. Langarudi, M. Seddighi, O.G. Jolodar, Res. Chem. Intermed. 41, 8483 (2015)

    Article  CAS  Google Scholar 

  35. S. Nazari, M. Keshavarz, B. Karami, N. Iravani, M. Vafaee-Nezhad, Chin. Chem. Lett. 25, 317 (2014)

    Article  CAS  Google Scholar 

  36. A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, J. Mol. Liq. 167, 69 (2012)

    Article  CAS  Google Scholar 

  37. N. Azizi, F. Abbasi, M. Abdoli-Senejani, ChemistrySelect 3, 3797 (2018)

    Article  CAS  Google Scholar 

  38. N. Azizi, F. Shirdel, J. Mol. Liq. 222, 783 (2016)

    Article  CAS  Google Scholar 

  39. 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 

  40. M. Nisar, I. Ali, M.R. Shah, A. Badshah, M. Qayum, H. Khan, I. Khan, S. Ali, RSC Adv. 3, 21753 (2013)

    Article  CAS  Google Scholar 

  41. S. Sadjadi, M.M. Heravi, M. Daraie, Res. Chem. Intermed. 43, 843 (2017)

    Article  CAS  Google Scholar 

  42. M. Rohaniyan, A. Davoodnia, S.A. Beyramabadi, A. Khojastehnezhad, Appl. Organomet. Chem. 33, e4881 (2019)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  44. Z. Abdi Piralghar, M. M. Hashemi, A. Ezabadi. Polycycl. Aromat. Compd. 1 (2019)

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  47. M. Puripat, R. Ramozzi, M. Hatanaka, W. Parasuk, V. Parasuk, K. Morokuma, J. Org. Chem. 80, 6959 (2015)

    Article  CAS  PubMed  Google Scholar 

  48. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  49. G.C. Tron, A. Minassi, G. Appendino, Eur. J. Org. Chem. 2011, 5541 (2011)

    Article  CAS  Google Scholar 

  50. G. Maiti, P. Kundu, C. Guin, Tetrahedron Lett. 44, 2757 (2003)

    Article  CAS  Google Scholar 

  51. A. Khorshidi, K. Tabatabaeian, H. Azizi, M. Aghaei-Hashjin, E. Abbaspour-Gilandeh, RSC Adv. 7, 17732 (2017)

    Article  CAS  Google Scholar 

  52. M. Brands, R. Endermann, R. Gahlmann, J. Krüger, S. Raddatz, Bioorgan. Med. Chem. Lett. 13, 241 (2003)

    Article  CAS  Google Scholar 

  53. B. Tozkoparan, M. Ertan, P. Kelicen, R. Demirdamar, Il Farmaco 54, 588 (1999)

    Article  CAS  PubMed  Google Scholar 

  54. G.J. Grover, S. Dzwonczyk, D.M. McMullen, D.E. Normandin, C.S. Parham, P.G. Sleph, S. Moreland, J. Cardiovasc. Pharmacol. 26, 289 (1995)

    Article  CAS  PubMed  Google Scholar 

  55. A. Debache, M. Amimour, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 49, 6119 (2008)

    Article  CAS  Google Scholar 

  56. U.K. Sharma, N. Sharma, R. Kumar, A.K. Sinha, Amino Acids 44, 1031 (2013)

    Article  CAS  PubMed  Google Scholar 

  57. T.M. Kapoor, T.U. Mayer, M.L. Coughlin, T.J. Mitchison, J. Cell Biol. 150, 975 (2000)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  58. Y. Yu, D. Liu, C. Liu, G. Luo, Bioorg. Med. Chem. Lett. 17, 3508 (2007)

    Article  CAS  PubMed  Google Scholar 

  59. B. Jauk, T. Pernat, C. Kappe, Molecules 5, 227 (2000)

    Article  CAS  Google Scholar 

  60. C.O. Kappe, J. Org. Chem. 62, 7201 (1997)

    Article  CAS  PubMed  Google Scholar 

  61. A. Crespo, A. El Maatougui, P. Biagini, J. Azuaje, A. Coelho, J. Brea, M.I. Loza, M.I. Cadavid, X. García-Mera, H. Gutiérrez-de-Terán, ACS Med. Chem. Lett. 4, 1031 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. B.C. O’Reilly, K.S. Atwal, Heterocycles 26, 1185 (1987)

    Article  Google Scholar 

  63. N.Y. Gorobets, Y.V. Sedash, K.S. Ostras, O.V. Zaremba, S.V. Shishkina, V.N. Baumer, O.V. Shishkin, S.M. Kovalenko, S.M. Desenko, E.V. Van der Eycken, Tetrahedron Lett. 51, 2095 (2010)

    Article  CAS  Google Scholar 

  64. J. Světlík, V. Kettmann, Tetrahedron Lett. 52, 1062 (2011)

    Article  CAS  Google Scholar 

  65. H. Cho, Y. Nishimura, Y. Yasui, S. Kobayashi, S.-I. Yoshida, E. Kwon, M. Yamaguchi, Tetrahedron 67, 2661 (2011)

    Article  CAS  Google Scholar 

  66. Z. Hassani, M.R. Islami, M. Kalantari, Bioorg. Med. Chem. Lett. 16, 4479 (2006)

    Article  CAS  PubMed  Google Scholar 

  67. T. Shu-Jiang, Z. Xiao-Tong, F. Fang, Z. Xiao-Jing, Z. Song-Lei, L. Tuan-Jie, S. Da-Qing, W. Xiang-Shan, J. Shun-Jun, Chin. J. Chem. 23, 596 (2005)

    Article  Google Scholar 

  68. L.M. Ramos, A.Y. Ponce de Leon y Tobio, M.R. dos Santos, H.C. de Oliveira, A.F. Gomes, F.C. Gozzo, A.L. de Oliveira, B.A. Neto, J. Org. Chem. 77, 10184 (2012)

    Article  CAS  PubMed  Google Scholar 

  69. O.M. Singh, N.S. Devi, J. Org. Chem. 74, 3141 (2009)

    Article  CAS  PubMed  Google Scholar 

  70. E.H. Hu, D.R. Sidler, U.-H. Dolling, J. Org. Chem. 63, 3454 (1998)

    Article  CAS  Google Scholar 

  71. M. Pramanik, A. Bhaumik, ACS Appl. Mater. Interfaces. 6, 933 (2014)

    Article  CAS  PubMed  Google Scholar 

  72. C.K. Khatri, D.S. Rekunge, G.U. Chaturbhuj, New J. Chem. 40, 10412 (2016)

    Article  CAS  Google Scholar 

  73. H.G. Alvim, T.B. de Lima, H.C. de Oliveira, F.C. Gozzo, J.L. de Macedo, P.V. Abdelnur, W.A. Silva, B.A. Neto, ACS Catal. 3, 1420 (2013)

    Article  CAS  Google Scholar 

  74. N. Sharma, U.K. Sharma, R. Kumar, A.K. Sinha, RSC Adv. 2, 10648 (2012)

    Article  CAS  Google Scholar 

  75. F. Dong, L. Jun, Z. Xinli, Y. Zhiwen, L. Zuliang, J. Mol. Catal. A: Chem. 274, 208 (2007)

    Article  CAS  Google Scholar 

  76. F. Heidarizadeh, E.R. Nezhad, S. Sajjadifar, Sci. Iran. 20, 561 (2013)

    CAS  Google Scholar 

  77. Q. Zhang, X. Wang, Z. Li, W. Wu, J. Liu, H. Wu, S. Cui, K. Guo, RSC Adv. 4, 19710 (2014)

    Article  CAS  Google Scholar 

  78. R.V. Patil, J.U. Chavan, D.S. Dalal, V.S. Shinde, A.G. Beldar, ACS Comb. Sci. 21, 105 (2019)

    Article  CAS  PubMed  Google Scholar 

  79. H.Z. Mohammad, S. Javanshir, B. Hemmati, Z. Dolatkhah, M. Fardpour, Chem. Cent. J. 12, 108 (2018)

    Article  CAS  Google Scholar 

  80. D.P. Narayanan, A. Gopalakrishnan, Z. Yaakob, S. Sugunan, B.N. Narayanan. Arab. J. Chem. 13, 318 (2020)

  81. M. Nasr-Esfahani, M. Taei, RSC Adv. 5, 44978 (2015)

    Article  CAS  Google Scholar 

  82. M. Sheykhan, A. Yahyazadeh, Z. Rahemizadeh, RSC Adv. 6, 34553 (2016)

    Article  CAS  Google Scholar 

  83. N.H. Thi Nguyen, P.P. Thi Nguyen, T.D. Thi Nguyen, M.N. Thi Tran, T.N. Thi Huynh, P.H. Tran, ChemistrySelect 2, 3932 (2017)

    Article  CAS  Google Scholar 

  84. J. Safari, S. Gandomi-Ravandi, New J. Chem. 38, 3514 (2014)

    Article  CAS  Google Scholar 

  85. A.R. Hajipour, M. Seddighi, Synth. Commun. 42, 227 (2012)

    Article  CAS  Google Scholar 

  86. A. Zhu, Q. Li, L. Li, J. Wang, Catal. Lett. 143, 463 (2013)

    Article  CAS  Google Scholar 

  87. A. Debache, R. Boulcina, R. Tafer, A. Belfaitah, S. Rhouati, B. Carboni, Chin. J. Chem. 26, 2112 (2008)

    Article  CAS  Google Scholar 

  88. F. Bigi, S. Carloni, B. Frullanti, R. Maggi, G. Sartori, Tetrahedron Lett. 40, 3465 (1999)

    Article  CAS  Google Scholar 

  89. H.R. Shaterian, A. Hosseinian, M. Ghashang, F. Khorami, N. Karimpoor, Phosphorus, Sulfur Silicon Relat. Elem. 184, 2333 (2009)

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Seyyed Erfan Sadati Sorkhi & Mohammad M. Hashemi

  2. Department of Chemistry, Faculty of Science, Central Tehran Branch, Islamic Azad University, Tehran, Iran

    Ali Ezabadi

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Sadati Sorkhi, S.E., Hashemi, M.M. & Ezabadi, A. Introduction of a novel dicationic Brönsted acidic ionic liquid based on pyrazine and its application in the synthesis of xanthenediones and 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. Res Chem Intermed 46, 2229–2246 (2020). https://doi.org/10.1007/s11164-020-04089-9

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