Skip to main content
SpringerLink
Log in

Novel synthesis of nano-amino acid-based ionic liquid and its application for preparing DHPMs and xanthenes under solvent-free conditions

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this study, glycine-based ionic liquid ([Gly-H][OTs]) was synthesized through a reaction of glycine with ρ-toluenesulfonic acid in water. The synthesized IL was utilized for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones, 14-aryl-14H-dibenzo[a,j]xanthenes and 12-aryl-8,9,10,12-tetrahydrobenzo [a]xanthene-11-ones under solvent-free condition. The prepared IL indicates desirable catalytic activity in organic reactions under solvent-free conditions with the high reusability of four runs. The proposed protocol's main advantages are the originality of prepared [Gly-H][OTs], organic green synthesis under solvent-free conditions, high product yields, and less reaction times.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 1
Fig. 8
Scheme 2
Scheme 3

Similar content being viewed by others

Data availability

Not applicable.

References

  1. T. Welton, Biophys. Rev. 10, 691 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. K. Sood, Y. Saini, K.K. Thakur, Mater. Today Proc. (2021 in press)

  3. M. Salami, A. Ezabadi, Polycycl. Aromat. Compd. 42, 3377 (2022)

    Article  CAS  Google Scholar 

  4. D. Liu, H. Wang, M. Liang, Y. Nie, Y. Liu, M. Yin, X. Qiao, J. Chromatogr. A 1660, 462676 (2021)

    Article  CAS  PubMed  Google Scholar 

  5. J.-M. Leveque, J. Estager, M. Draye, G. Cravotto, L. Boffa, W. Bonrath, Monatsh. Fur Chem. 138, 1103 (2007)

    Article  CAS  Google Scholar 

  6. D.A. Waterkamp, M. Heiland, M. Schlüter, J.C. Sauvageau, T. Beyersdorff, J. Thöming, Green Chem. 9, 1084 (2007)

    Article  CAS  Google Scholar 

  7. Z. Radai, N.Z. Kiss, G. Keglevich, Curr. Org. Chem. 22, 533 (2018)

    Article  CAS  Google Scholar 

  8. Z. Yang, C. Sun, C. Zhang, S. Zhao, M. Cai, Z. Liu, Q. Yu, Tribol. Int. 153, 106663 (2021)

    Article  CAS  Google Scholar 

  9. Y. Qu, J. Lan, Y. Chen, J. Sun, Sustain. Energy Fuels 5, 2494 (2021)

    Article  CAS  Google Scholar 

  10. R. Aslam, M. Mobin, M. Murmu, P. Banerjee, J. Aslam, J. Mol. Liq. 334, 116469 (2021)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. V.V. Chaban, E.E. Fileti, (2014)

  13. A.S. Amarasekara, Chem. Rev. 116, 6133 (2016)

    Article  CAS  PubMed  Google Scholar 

  14. H. Olivier-Bourbigou, L. Magna, D. Morvan, Appl. Catal. A-Gen. 373, 1 (2010)

    Article  CAS  Google Scholar 

  15. K. Lam, H. Timmerman, Drug Discov. Today Technol. 29, 103420 (2018)

    Google Scholar 

  16. S. Javanbakht, A. Shaabani, A.C.S. Appl, Bio Mater. 3, 156 (2019)

    Google Scholar 

  17. S. Zhi, X. Ma, W. Zhang, Org. Biomol. Chem. 17, 7632 (2019)

    Article  CAS  PubMed  Google Scholar 

  18. O. Soleimani, J. Chem. Rev. 2, 169 (2020)

    CAS  Google Scholar 

  19. L.H.S. Matos, F.T. Masson, L.A. Simeoni, M. Homem-de-Mello, Eur. J. Med. Chem. 143, 1779 (2018)

    Article  CAS  PubMed  Google Scholar 

  20. N.C. Desai, S.B. Joshi, K.A. Jadeja, J. Heterocycl. Chem. 57, 791 (2020)

    Article  CAS  Google Scholar 

  21. A.N. Panaskar, A. Jain, P.K. Mohanty, J. Pharm. Res. Int. 33, 481 (2021)

    Article  Google Scholar 

  22. K. Jeena-Thomas, M. George, L. Joseph, J. Chem. Res. 4, 19 (2019)

    Google Scholar 

  23. J. Dowarah, D. Patel, B.N. Marak, U.C.S. Yadav, P.K. Shah, P.K. Shukla, V.P. Singh, RSC Adv. 11, 35737 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. E. Guantai, K. Chibale, Curr. Drug Deliv. 7, 312 (2010)

    Article  CAS  PubMed  Google Scholar 

  25. K.M. Bairagi, N.S. Younis, P.M. Emeka, E. Sangtani, R.G. Gonnade, K.N. Venugopala, O.I. Alwassil, H.E. Khalil, S.K. Nayak, Med. Chem. 16, 996 (2020)

    Article  CAS  PubMed  Google Scholar 

  26. B. Gawdzik, P. Kowalczyk, D. Koszelewski, A. Brodzka, J. Masternak, K. Kramkowski, A. Wypych, R. Ostaszewski, Membranes 12, 238 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. C.O. Kappe, Q.S.A.R. Comb, Sci. 22, 630 (2003)

    CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  29. C.O. Kappe, Tetrahedron 49, 6937 (1993)

    Article  CAS  Google Scholar 

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

    Google Scholar 

  31. N.D. Kadam, R.V. Jayaram, Curr. Catal. 7, 52 (2018)

    Article  CAS  Google Scholar 

  32. M. Aalam, S. Singh, ChemistrySelect 7, 202103918 (2022)

    Google Scholar 

  33. B.-J. Yao, W.-X. Wu, L.-G. Ding, Y.-B. Dong, J. Org. Chem. 86, 3024 (2021)

    Article  CAS  PubMed  Google Scholar 

  34. M. Kaur, D. Bains, G. Singh, N. Kaur, N. Singh, Polym. Chem. 12, 1165 (2021)

    Article  CAS  Google Scholar 

  35. S. Ghosh, N. Nagarjun, S. Nandi, A. Dhakshinamoorthy, S. Biswas, J. Mater. Chem. C 10, 6717 (2022)

    Article  CAS  Google Scholar 

  36. M.R. Maurya, A. Chauhan, S. Arora, P. Gupta, Catal. Today 379–399, 3 (2022)

    Article  Google Scholar 

  37. R. Singh, in Applications of nanotechnology for green synthesis, (Springer, 2020), p. 60

  38. D. Fazzi, C. Castiglioni, F. Negri, Phys. Chem. Chem. Phys. 12, 1600 (2010)

    Article  CAS  PubMed  Google Scholar 

  39. X. Guo, X.-R. Wei, R. Sun, Y.-J. Xu, Y. Chen, J.-F. Ge, Sens. Actuators B Chem. 296, 126621 (2019)

    Article  CAS  Google Scholar 

  40. G. Shabir, A. Saeed, P. Ali Channar, Mini Rev. Org. Chem. 15, 166 (2018)

    Article  CAS  Google Scholar 

  41. T. Bezrodna, V. Bezrodnyi, A. Negriyko, L. Kosyanchuk, O. Antonenko, Macromol. Symp. 396, 2000232 (2021)

    Article  Google Scholar 

  42. M. Pishgar, K. Gharanjig, M. Yazdanshenas, K. Farizadeh, A. Rashidi, Prog. Color. Color. Coat. 15, 87 (2022)

    CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  44. H. Naeimi, Z. Ansarian, J. Taiwan Inst. Chem. Eng. 85, 265 (2018)

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  46. H. Faroughi Niya, N. Hazeri, M. Fatahpour, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 3651 (2020)

    Article  CAS  Google Scholar 

  47. A. Marandi, N. Koukabi, M.A. Zolfigol, Res. Chem. Intermed. 47, 3145 (2021)

    Article  CAS  Google Scholar 

  48. M. Zabihzadeh, F. Shirini, H. Tajik, N. Daneshvar, Polycycl. Aromat. Compd. 1, 2052 (2020)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  50. W. Abo El-Yazeed, O. Hayes, A.I. Ahmed, J. Sol–Gel Sci. Technol. 99, 140 (2021)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  54. R. Manepalli, G. Giridhar, P. Pardhasaradhi, P. Jayaprada, M. Tejaswi, K. Sivaram, C.M. Kumar, V. Pisipati, Mater. Today Proc. 5, 2666 (2018)

    Article  CAS  Google Scholar 

  55. S. Saikia, R. Borah, ChemSelect 4, 8751 (2019)

    CAS  Google Scholar 

  56. L. Ouyang, T. Zheng, L. Shen, Cryst. Eng. Commun. 20, 2705 (2018)

    Article  CAS  Google Scholar 

  57. Z. Karimi-Jaberi, M.S. Moaddeli, ISRN Org. Chem. 2012, 2154 (2012)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  60. M. Salami, A. Ezabadi, Polycycl. Aromat. Compd. 1, 1245 (2020)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  62. F. Shirini, M. Abedini, M. Seddighi, O.G. Jolodar, M. Safarpoor, N. Langroodi, S. Zamani, RSC Adv. 4, 63526 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  64. H. Valizadeh, A. Shockravi, Heteroat. Chem. Int. J. Main Group Elem. 20, 284 (2009)

    CAS  Google Scholar 

  65. B. Pouramiri, R. Fayazi, E. Tavakolinejad-Kermani, Iran. J. Chem. Chem. Eng. (IJCCE) 37, 159 (2018)

    CAS  Google Scholar 

  66. Z. Liu, R. Ma, D. Cao, C. Liu, Molecules 21, 462 (2016)

    Article  PubMed  PubMed Central  Google Scholar 

  67. D. Fang, Z.L. Liu, J. Heterocycl. Chem. 47, 509 (2010)

    CAS  Google Scholar 

  68. K. Gong, D. Fang, H.-L. Wang, X.-L. Zhou, Z.-L. Liu, Dyes Pigm. 80, 30 (2009)

    Article  CAS  Google Scholar 

  69. H. Naeimi, Z.S. Nazifi, C. R. Chim. 17, 41 (2014)

    Article  CAS  Google Scholar 

  70. M. Zakeri, M.M. Heravi, M. Saeedi, N. Karimi, H.A. Oskooie, N. Tavakoli-Hoseini, Chin. J. Chem. 29, 1441 (2011)

    Article  CAS  Google Scholar 

  71. X.-D. Jia, S.-Y. Han, H.-F. Duan, Y.-J. Lin, J.-G. Cao, D.-P. Liang, M.-C. Wu, Chem. Res. Chin. Univ. 29, 82 (2013)

    Article  CAS  Google Scholar 

  72. H. Singh, S. Kumari, J.M. Khurana, Chin. Chem. Lett. 25, 1336 (2014)

    Article  CAS  Google Scholar 

Download references

Funding

Not applicable.

Author information

Authors and Affiliations

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

    Elaheh Hataminejad & Ali Ezabadi

  2. Department of Chemistry, Omidiyeh Branch, Islamic Azad University, Omidiyeh, Iran

    Abolghasem Shameli Akandi

Authors
  1. Elaheh Hataminejad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ali Ezabadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abolghasem Shameli Akandi
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

AE contributed to conceptualization, design the experiment, supervision, formal analysis, validation, and critical revision of the article. EH contributed to performing the experiment, data acquisition, formal analysis, initial draft, and revision of the article. ASA contributed to consulting on performing the experiment and revision of the article.

Corresponding author

Correspondence to Ali Ezabadi.

Ethics declarations

Conflict of interest

There are no conflict of interest.

Ethical approval

Not applicable.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hataminejad, E., Ezabadi, A. & Shameli Akandi, A. Novel synthesis of nano-amino acid-based ionic liquid and its application for preparing DHPMs and xanthenes under solvent-free conditions. Res Chem Intermed 49, 1275–1295 (2023). https://doi.org/10.1007/s11164-022-04931-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04931-2

Keywords

Search

Navigation