10.57647/j.ijc.2025.1502.18

Ionic Liquid-mediated Multi-component Reaction Towards the Synthesis of Dihydropyrimidones: An Environmentally Benign Green Protocol

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  • Rakesh P. Chaudhari1,
  • Ganesh R. Chaudhari1,
  • Hemant A. Mahajan2,
  • Harish R. Talele3,
  1. Department of Chemistry, Arts and Science College, Bhalod, Dist. – Jalgaon, Maharashtra, India
  2. Department of Chemistry, Smt. G. G. Khadse College, Muktainagar, Dist. – Jalgaon, Maharashtra, India
  3. Department of Chemistry, TVES’s Dhanaji Nana Mahavidyalaya, Faizpur, Dist. – Jalgaon, Maharashtra, India

Received: 2024-03-08

Revised: 2024-07-10

Accepted: 2025-04-21

Published in Issue 2025-05-03

Copyright (c) -1 Rakesh P. Chaudhari, Ganesh R. Chaudhari, Hemant A. Mahajan, Harish R. Talele (Author)

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This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Chaudhari, R. P., Chaudhari, G. R., Mahajan, H. A., & Talele, H. R. (2025). Ionic Liquid-mediated Multi-component Reaction Towards the Synthesis of Dihydropyrimidones: An Environmentally Benign Green Protocol. Iranian Journal of Catalysis, 15(2 (June 2025). https://doi.org/10.57647/j.ijc.2025.1502.18
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Abstract

Multi-component reaction (MCR) has notable benefits when compared to traditional linear-type synthetic methods, owing to its adaptable, convergent, and atom-efficient properties. Herein, this study reported the three-component reaction using ethylacetoacetate, aldehydes, and urea in one-step synthesis that provided the 3,4-dihydropyrimidin-2(1H)-ones in excellent yields, such as 5-(Ethoxycarbonyl)-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one obtained up to 94% of yield.  The conversion was led by a catalytic amount of sulfuric acid and ionic liquids as a recyclable green solvent at 80 °C. The recyclable activity of the catalytic system up to three cycles shows excellent yields, ranging from 88% to 94%.

Research Highlights:

  • The manuscript reports synthesis of the dihydropyrimidone derivatives by a catalytic system conc. H2SO4 in Ionic Liquids.
  • Introduce the environment friendly protocol for the synthesis of dihydropyrimidones derivatives.  
  • The presented method following the advantages: short reaction time, mild reaction conditions, and high yields.
  • The synthesized compounds were characterized by FT-IR, 1H/13C NMR, and Mass analysis.

Keywords

  • Ionic Liquid (ILs),
  • Imidazolinium ionic liquids,
  • Pyridinium ionic liquids,
  • Dihydropyrimidinones
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References

  1. E. V. Van der Eycken, U. K. Sharma, Multicomponent Reactions towards Heterocycles: Concepts and Applications, Wiley-VCH GmbH, Germany, 2022. doi: 10.1002/9783527832439
  2. R. P. Herrera, E. Marqués‐López, Multicomponent Reactions: Concepts and Applications for Design and Synthesis, John Wiley & Sons, Inc., Hoboken, New Jersey, 2015. doi: 10.1002/9781118863992
  3. A. DomLing, Chem. Rev., 106 (2005) 17–89. doi:10.1021/cr0505728
  4. L. Weber, Drug Discov. Today, 7, (2002), 143–147. doi:10.1016/S1359-6446(01)02090-6
  5. I. K. Ugi, Pure Appl. Chem., Vol. 73, (2001) No. 1, pp. 187–191. doi:10.1351/pac200173010187
  6. R. C. Cioc, E. Ruijter, R. V. A. Orru, Green Chem. 16 (2014) 2958–2975. doi:10.1039/C4GC00013G
  7. Q. Guan, L.-L. Zhou, Y-B. Dong, Jour. Am. Chem. Soc., 145 (2023) 1475–1496. doi: 1021/jacs.2c11071
  8. M. P. Parmar, R. M. Vala, H. M. Patel, ACS Omega, 8 (2023) 1759–1816. doi:10.1021/acsomega.2c05349
  9. M. G. Sharma, R. M. Vala, D. P. Rajani, V. Ramkumar, R. L. Gardas, S. Banerjee, H. M. Patel, Phosphorus, Sulfur, and Silicon and the Related Elements, 198 (2023) 145-153. doi:10.1080/10426507.2022.2121397
  10. R. M. Vala, M. G. Sharma, D. M. Patel, A. Puerta, J. M. Padrón, V. Ramkumar, R. L. Gardas, H. M. Patel, Arch Pharm, 354 (2021) 2000466. doi:10.1002/ardp.202000466
  11. J. Zhuang, S. Ma, ChemMedChem, 15 (2020) 1875–1886. doi:10.1002/cmdc.202000378
  12. A. Baqi, R. N. Talib, A. Ali, Res. Jour. Pharm. and Tech., (2023) 1289–1295. doi:10.52711/0974-360X.2023.00212
  13. K. Ahmed, M. Iqbal Choudhary, R. S. Z. Saleem, Eur. J. Med. Chem., 259 (2023) 115701. doi: 10.1016/j.ejmech.2023.115701
  14. P. S. Sidat, M. Kasim, S. R. Vekariya, A. M. Mogal, A. M. Patel, M. N. Noolvi, Pharmacophore, 13 (2022) 59–71. doi:10.51847/rT6VE6gESu
  15. M. A. H. Shallal, Egypt. J. Chem., 66 (2022) 41–49. doi:10.21608/ejchem.2022.154542.6675
  16. I. M. Lagoja, Chem. Biodiversity, 2 (2005) 1–50. doi:10.1002/cbdv.200490173
  17. A. Thawabteh, S. Juma, M. Bader, D. Karaman, L. Scrano, S. A. Bufo, R. Karaman, Toxins, 11, (2019) 656 (1-28). doi:10.3390/toxins11110656
  18. M. F. C. Santos, P. M. Harper, D. E. Williams, J. T. Mesquita, É. G. Pinto, T. A. da Costa-Silva, E. Hajdu, A. G. Ferreira, R. A. Santos, P. J. Murphy, R. J. Andersen, A. G. Tempone, R. G. S. Berlinck, J. Nat. Prod., 78 (2015) 1101–1112. doi:10.1021/acs.jnatprod.5b00070
  19. R. Kaur, S. Chaudhary, K. Kumar, M. K. Gupta, R. K. Rawal, Eur. J. Med. Chem., 132 (2017) 108–134. doi:10.1016/j.ejmech.2017.03.025
  20. M. Castro Jara, A. C. A. Silva, M. Ritter, A. F. da Silva, C. L. Gonçalves, P. R. dos Santos, L. S. Borja, C. M. P. de Pereira and P. da Silva Nascente, Front. Microbiol., 13 (2022) 1–9. doi:10.3389/fmicb.2022.743213
  21. M. Nisar, H. Y. Gondal, S. Munir, Z. M. Cheema, S. A. Al‐Hussain, A. Zaki, J. Saudi Chem. Soc., 27 (2023) 101687–101687. doi:10.1016/j.jscs.2023.101687
  22. P. Patil, S. M. Kadam, D. Patil, P. More, Catal. Commun., 170 (2022) 106500–106500. doi:10.1016/j.catcom.2022.106500
  23. S. Nagarajan, T. M. Shaikh, K. Elango, J. Chem. Sci., 127 (2015) 1539–1545. doi:10.1007/s12039-015-0919-6
  24. R. Fu, Y. Yang, W. Lai, Y. Ma, Z. Chen, J. Zhou, W. Chai, Q. Wang, R. Yuan, Synthetic Commun., 45 (2014) 467–477. doi:10.1080/00397911.2014.976346
  25. D. Elhamifar, M. Nasr-Esfahani, B. Karimi, R. Moshkelgosha, A. Shábani, ChemCatChem, 6 (2014) 2593–2599. doi:10.1002/cctc.201402162
  26. D. Elhamifar, A. Shábani, Chem. A Eur. Jour. 20 (2014) 3212–3217. doi:10.1002/chem.201304349
  27. D. Elhamifar, E. Nazari, ChemPlusChem, 80 (2015) 820–826. doi:10.1002/cplu.201402415
  28. A. Pourjavadi, S. H. Hosseini, R. Soleyman, J. Mol. Catal. A-Chem., 365 (2012) 55–59. doi:10.1016/j.molcata.2012.08.008
  29. R. Velpula, J. Banothu, R. Gali, R. Deshineni, R. Bavantula, Chinese Chem. Lett., 26 (2015) 309–312. doi:10.1016/j.cclet.2014.11.030
  30. A. Ncube, S. Mtetwa, M. Bukhari, G. Fiorentino, R. Passaro, Energies, 16 (2023) 1752 (1-21). doi:10.3390/en16041752
  31. O. B. Ghanem, S. Raja, S. N. Shah, M. I. A. Mutalib, J–M Lévêque, Z. Ullah, M. El‐Harbawi, M. S. Alnarabiji, Fuel, 337 (2023) 127141–127141. doi:10.1016/j.fuel.2022.127141
  32. P. T. Anastas, E. S. Beach, Green Chem. Lett. Rev., 1 (2007) 9–24. doi:10.1080/17518250701882441
  33. T. Welton, Biophys. Rev., 10 (2018) 691–706. doi:10.1007/s12551-018-0419-2
  34. B. Tong, Q.-S. Liu, Z.-C. Tan, U. Welz-Biermann, J. Phy. Chem. A, 114 (2010) 3782–3787. doi:10.1021/jp9047538
  35. Yassine Chaker a, b, Hocine Ilikti a, Mansour Debdab b, Taqiyeddine Moumene b, El Habib Belarbi b, Anne Wadouachi c, Ouissam Abbas d, Brahim Khelifa e, Serge Bresson, Jour. Mol. Struct. 1113 (2016) 182-190. doi:10.1016/j.molstruc.2016.02.017
  36. F. R. Gomari, S. Farahi, H. A. Nezhad, Iran. J. Chem. Chem. Eng., 1 (2021) 888-897. doi:10.30492/ijcce.2020.38166
  37. H. S. Oboudatian, H. Naeimi, M. Moradian, RSC Adv., 11 (2021) 7271–7279. doi:10.1039/D0RA09929E
  38. B. Mohammadi, F. K. Behbahani, G. B. Marandi, B. Mirza, Phosphorus, Sulfur, and Silicon and the Related Elements, 196 (2020) 54–60. doi:10.1080/10426507.2020.1800702
  39. L. Zheng, Y. Wang, Y. Li, W. Zhang, Chinese J. Org. Chem., 42 (2022) 3714–3714. doi:10.6023/cjoc202206002