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Introduction of two novel biocompatible deep eutectic mixtures for the promotion of the green synthesis of triazoloquinazolines: a comparative study

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Abstract

In this study, two new deep eutectic mixtures were prepared via combination of D-fructose with urea and L-aspartic acid or L-arginine. After identification, the catalytic activity of these mixtures, was evaluated in the one-pot multi-component synthesis of tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)-one derivatives. In the presence of both prepared mixtures the desired products were obtained with high diversity from the reaction of 3-amino-1,2,4-triazole, aromatic aldehydes and dimedone or cyclohexanedione in short reaction times with good yields. The reported methods have notable features such as easy preparation of the catalysts, green processes, cost-effectiveness and simple work-up procedures. Addintionally, the catalysts are easily recoverable and can be recycled up to five times without substantial loss of their activity.

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All data generated or analyzed during this study are included in this published article [and its supplementary information files].

References

  1. A. Gałuszka, Z. Migaszewski, J. Namieśnik, Trends Anal. Chem. 50, 78 (2013)

    Google Scholar 

  2. M. Himaja, D. Poppy, K. Asif, Int. J. Res. Ayurveda Pharm. 2, 1079 (2011)

    CAS  Google Scholar 

  3. K. Tekin, N. Hao, S. Karagoz, A.J. Ragauskas, Chemsuschem 11, 3559 (2018)

    CAS  PubMed  Google Scholar 

  4. X. Yang, K. Odelius, M. Hakkarainen, A.C.S. Sustain, Chem. Eng. 2, 2198 (2014)

    CAS  Google Scholar 

  5. H. Vanda, Y. Dai, E.G. Wilson, R. Verpoorte, Y.H. Choi, C. R. Chim. 21, 628 (2018)

    CAS  Google Scholar 

  6. J. Sperry, J. García-Álvarez, Molecules 21, 1527 (2016)

    PubMed  PubMed Central  Google Scholar 

  7. R. Craveiro, I. Aroso, V. Flammia, T. Carvalho, M. Viciosa, M. Dionísio, S. Barreiros, R. Reis, A.R.C. Duarte, A. Paiva, J. Mol. Liq. 215, 534 (2016)

    CAS  Google Scholar 

  8. A. Paiva, R. Craveiro, I. Aroso, M. Martins, R.L. Reis, A.R.C. Duarte, A.C.S. Sustain, Chem. Eng. 2, 1063 (2014)

    CAS  Google Scholar 

  9. A.P. Abbott, G. Capper, D.L. Davies, H.L. Munro, R.K. Rasheed, V. Tambyrajah, ChemComm. 1, 2010 (2001)

    Google Scholar 

  10. M. Jablonský, A. Škulcová, J. Šima, Molecules 24, 3978 (2019)

    PubMed  PubMed Central  Google Scholar 

  11. M. Atilhan, S. Aparicio, J. Phys. Chem. C. 120, 10400 (2016)

    CAS  Google Scholar 

  12. Y. Dai, G.-J. Witkamp, R. Verpoorte, Y.H. Choi, Anal. Chem. 85, 6272 (2013)

    CAS  PubMed  Google Scholar 

  13. K.H. Kim, T. Dutta, J. Sun, B. Simmons, S. Singh, Green Chem. 20, 809 (2018)

    CAS  Google Scholar 

  14. D. González-Martínez, V. Gotor, V. Gotor-Fernández, Eur. J. Org. Chem. 2016, 1513 (2016)

    Google Scholar 

  15. D.J. van Osch, L.F. Zubeir, A. van den Bruinhorst, M.A. Rocha, M.C. Kroon, Green Chem. 17, 4518 (2015)

    Google Scholar 

  16. A.E. Ünlü, A. Arıkaya, S. Takaç, Green Process. Synth. 8, 355 (2019)

    Google Scholar 

  17. J.-S. Lee, Nanotechnol. Rev. 6, 271 (2017)

    CAS  Google Scholar 

  18. P. Liu, J.-W. Hao, L.-P. Mo, Z.-H. Zhang, RSC Adv. 5, 48675 (2015)

    CAS  Google Scholar 

  19. W.-H. Zhang, M.-N. Chen, Y. Hao, X. Jiang, X.-L. Zhou, Z.-H. Zhang, J. Mol. Liq. 278, 124 (2019)

    CAS  Google Scholar 

  20. G. Gao, P. Wang, P. Liu, W. Zhang, L. Mo, Z. Zhang, Chin. J. Org. Chem. 38, 846 (2018)

    CAS  Google Scholar 

  21. M. Zhang, Y.-H. Liu, Z.-R. Shang, H.-C. Hu, Z.-H. Zhang, Catal. Commun. 88, 39 (2017)

    CAS  Google Scholar 

  22. J. Zhang, S. Li, L. Yao, Y. Yi, L. Shen, Z. Li, H. Qiu, Chin. Chem. Lett. 34, 107750 (2023)

    CAS  Google Scholar 

  23. Y. Dai, J. Van Spronsen, G.-J. Witkamp, R. Verpoorte, Y.H. Choi, J. Nat. Prod. 76, 2162 (2013)

    CAS  PubMed  Google Scholar 

  24. M. Faggian, S. Sut, B. Perissutti, V. Baldan, I. Grabnar, S. Dall’Acqua, Molecules. 21, 1531 (2016)

  25. L.P. Silva, L. Fernandez, J.H. Conceição, M.A. Martins, A. Sosa, J. Ortega, S.P. Pinho, J.A. Coutinho, A.C.S. Sustain, Chem. Eng. 6, 10724 (2018)

    CAS  Google Scholar 

  26. A. Hayyan, F.S. Mjalli, I.M. AlNashef, T. Al-Wahaibi, Y.M. Al-Wahaibi, M.A. Hashim, Thermochim. Acta. 541, 70 (2012)

    CAS  Google Scholar 

  27. M.A. Khoshdel, F. Shirini, M.S.N. Langarudi, M. Zabihzadeh, M. Biglari, New J. Chem. 45, 3138 (2021)

    Google Scholar 

  28. F.S. Mjalli, J. Taiwan Inst. Chem. 61, 64 (2016)

    CAS  Google Scholar 

  29. F.S. Mjalli, R. Al‐Hajri, A.a. Al‐Muhtaseb, O. Ahmed, M. Nagaraju, Asia-Pac. J. Chem. Eng. 11, 683 (2016).

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

    CAS  PubMed  Google Scholar 

  31. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457 (2007)

    CAS  PubMed  Google Scholar 

  32. V. Alagarsamy, G. Murugananthan, R. Venkateshperumal, Biol. Pharm. Bull. 26, 1711 (2003)

    CAS  PubMed  Google Scholar 

  33. M.-J. Hour, L.-J. Huang, S.-C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.-H. Lee, J. Med. Chem. 43, 4479 (2000)

    CAS  PubMed  Google Scholar 

  34. V. Alagarsamy, R. Revathi, S. Meena, K. Ramaseshu, S. Rajasekaran, E. De Clerco, Indian J. Pharm. Sci. 66, 459 (2004)

    CAS  Google Scholar 

  35. K. Kumari, D. Raghuvanshi, K.N. Singh, Org. Prep. Proced. Int. 44, 460 (2012)

    CAS  Google Scholar 

  36. R. Bakhshali-Dehkordi, M.A. Ghasemzadeh, J. Safaei-Ghomi, Appl. Organomet. Chem. 34, 5721 (2020)

    Google Scholar 

  37. M.A. Kareem, F.S. Mjalli, M.A. Hashim, I.M. AlNashef, J. Chem. Eng. Data. 55, 4632 (2010)

    CAS  Google Scholar 

  38. M. Ibrahim, M. Alaam, H. El-Haes, A.F. Jalbout, A.d. Leon, Eclet. Quim. 31, 15 (2006).

  39. J.-J. Max, C. Chapados, J. Phys. Chem. A. 111, 2679 (2007)

    CAS  PubMed  Google Scholar 

  40. N. Delgado-Mellado, M. Larriba, P. Navarro, V. Rigual, M. Ayuso, J. García, F. Rodríguez, J. Mol. Liq. 260, 37 (2018)

    CAS  Google Scholar 

  41. D.A. Türker, M. Doğan, LWT - Food Sci. Technol. 138, 110775 (2021)

    Google Scholar 

  42. A.P. Abbott, G. Capper, S. Gray, ChemPhysChem 7, 803 (2006)

    CAS  PubMed  Google Scholar 

  43. M.M. Heravi, F. Derikvand, L. Ranjbar, Synth. Commun. 40, 677 (2010)

    CAS  Google Scholar 

  44. A. Shaabani, E. Farhangi, A. Rahmati, Comb. Chem. High Throughput Screen. 9, 771 (2006)

    CAS  PubMed  Google Scholar 

  45. M. Haghighat, F. Shirini, M. Golshekan, J. Mol. Struct. 1171, 168 (2018)

    CAS  Google Scholar 

  46. R.G. Puligoundla, S. Karnakanti, R. Bantu, K. Nagaiah, S.B. Kondra, L. Nagarapu, Tetrahedron Lett. 54, 2480 (2013)

    CAS  Google Scholar 

  47. H. Sharghi, J. Aboonajmi, M. Aberi, P. Shiri, J. Iran. Chem. Soc. 15, 1107 (2018)

    CAS  Google Scholar 

  48. I.M. Moghaddampour, F. Shirini, M.S.N. Langarudi, J. Mol. Struct. 1226, 129336 (2021)

    CAS  PubMed  Google Scholar 

  49. M.M. Heravi, L. Ranjbar, F. Derikvand, B. Alimadadi, H.A. Oskooie, F.F. Bamoharram, Mol. Divers. 12, 181 (2008)

    CAS  PubMed  Google Scholar 

  50. N. Seyyedi, F. Shirini, M.S.N. Langarudi, J. Iran. Chem. Soc. 14, 1859 (2017)

    CAS  Google Scholar 

  51. K.A. Shaikh, S.R. Kande, C. Khillare, IOSR, J. Appl. Chem. 7, 54 (2014)

    Google Scholar 

  52. A. Petrov, A. Kasatochkin, Russ. J. Org. Chem. 50, 1485 (2014)

    CAS  Google Scholar 

  53. Z. Alishahi, M. Torabi, M.A. Zolfigol, M. Yarie, J. Solid State Chem. 324, 124119 (2023)

    CAS  Google Scholar 

  54. N. Safari, F. Shirini, H. Tajik, J. Mol. Struct. 1201, 127143 (2020)

    CAS  Google Scholar 

  55. V. Lipson, S. Desenko, M. Shirobokova, V. Borodina, Chem. Heterocycl. Compd. 39, 1213 (2003)

    CAS  Google Scholar 

  56. M.R. Mousavi, M.T. Maghsoodlou, Monatsh. Chem. 145, 1967 (2014)

    CAS  Google Scholar 

  57. M.R. Mousavi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, J. Iran. Chem. Soc. 12, 1419 (2015)

    CAS  Google Scholar 

  58. S. Vibhute, D. Jamale, S. Undare, N. Valekar, G. Kolekar, P. Anbhule, Res. Chem. Intermed. 43, 4561 (2017)

    CAS  Google Scholar 

  59. G. Krishnamurthy, K. Jagannath, J. Chem. Sci. 125, 807 (2013)

    CAS  Google Scholar 

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Acknowledgements

The help of the Research Council of Guilan University in doing this work is acknowledged.

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All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by SY and FS. The first draft of the manuscript was written by SY and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Farhad Shirini.

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Yazdanfar, S., Shirini, F. Introduction of two novel biocompatible deep eutectic mixtures for the promotion of the green synthesis of triazoloquinazolines: a comparative study. Res Chem Intermed 49, 5205–5220 (2023). https://doi.org/10.1007/s11164-023-05132-1

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