Skip to content
2000
Volume 23, Issue 1
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

A series of 4-(((8-hydroxyquinolin-7-yl)(phenyl)methyl)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3-pyrazol-3-one derivatives were synthesized a one-pot, three-component reaction. The reaction employed benzaldehyde derivatives , 4-aminoantipyrine , and 8-hydroxyquinoline , using titanium dioxide nanoparticles (TiO NPs) as a catalyst. The TiO NPs, synthesized through a sol–gel method, efficiently catalyzed the transformation under mild conditions, delivering high yields in just 9 minutes at room temperature. Optimization revealed that 0.010 g of catalyst in methanol was optimal, with protic solvents outperforming aprotic and non-polar ones. The reaction progress was monitored using thin-layer chromatography (TLC), and the final products were isolated recrystallization. A systematic study of reaction parameters confirmed TiO NPs as an efficient, reusable, and environmentally friendly catalyst for multicomponent organic synthesis.

Loading

Article metrics loading...

/content/journals/loc/10.2174/0115701786406873250730182802
2025-08-07
2026-03-01
Loading full text...

Full text loading...

References

  1. Sol-MagdalenoM. Aguilar-AguilarJ.I. Beltrán-NaturiE. Valencia-OrdóñezL.D. Díaz-GonzálezA. Trejo-FloresP. Camas-FloresC.A. Palacios-PolaG. Ali-SahitoZ. González-MoscosoM. Discover Soil2025212610.1007/s44378‑025‑00054‑3
    [Google Scholar]
  2. ShenX. HongG. WangL. Org. Biomol. Chem.20252392059207810.1039/D4OB01822B 39887261
    [Google Scholar]
  3. YounusH.A. Al-RashidaM. HameedA. UroosM. SalarU. RanaS. KhanK.M. Expert Opin. Ther. Pat.202131326728910.1080/13543776.2021.1858797 33275061
    [Google Scholar]
  4. MustafaG. Zia-ur-RehmanM. SumrraS.H. J. Mol. Struct.2022126213304410.1016/j.molstruc.2022.133044
    [Google Scholar]
  5. KasareM.S. DhavanP.P. ShaikhA.H.I. JadhavB.L. PawarS.D. J. Mol. Recognit.2022359e297610.1002/jmr.2976 35569113
    [Google Scholar]
  6. Adithya KrishnanM. SaranyaparvathiS. RakshaC. VrindaB. GirishC.G. KulkarniN.V. KharisovB.I. Russ. J. Coord. Chem.2022481169672410.1134/S1070328422110082
    [Google Scholar]
  7. RenH. DhanarajP. EnochI.V.M.V. PaulrajM.S. MI. Med. Chem.2022181263510.2174/1573406416666201106105303 33155926
    [Google Scholar]
  8. NguyenL.H.T. TranK.D.H. LeT.M.T. NguyenV.P. VuG.B.N. TranP.H. UngT.D.T. PhamA.T.T. TranN.Q. Le MinhT. DoanT.L.H. Mater. Chem. Phys.202431912934610.1016/j.matchemphys.2024.129346
    [Google Scholar]
  9. RbaaM. HaidaS. TuzunB. hicharA. HassaneA.E. KribiiA. LakhrissiY. HaddaT.B. ZarroukA. LakhrissiB. BerdimurodovE. J. Mol. Struct.2022125813268810.1016/j.molstruc.2022.132688
    [Google Scholar]
  10. ZhangY. YangJ. MengT. QinY. LiT. FuJ. YinJ. Eur. J. Med. Chem.202121211315310.1016/j.ejmech.2021.113153 33453603
    [Google Scholar]
  11. WangD. LiS.J. CaoW. WangZ. MaY. ACS Omega2022721180171802610.1021/acsomega.2c01414 35664592
    [Google Scholar]
  12. RouifiZ. RbaaM. ErrahmanyN. SeghiriR. WaradI. OuddaH. LakhrissiB. BerdimurodovE. AlievN. ZarroukA. J. Dispers. Sci. Technol.202411410.1080/01932691.2024.2380035
    [Google Scholar]
  13. MohanramI. MeshramJ. ISRN Org. Chem.2014201411710.1155/2014/639392 24955256
    [Google Scholar]
  14. OsmanA.I. AyatiA. KrivoshapkinP. TanhaeiB. FarghaliM. YapP.S. AbdelhaleemA. Coord. Chem. Rev.202451421590010.1016/j.ccr.2024.215900
    [Google Scholar]
  15. GhobadiM. Kargar RaziM. JavahershenasR. KazemiM. Synth. Commun.202151564766910.1080/00397911.2020.1819328
    [Google Scholar]
  16. RajaramP. JeiceA.R. JayakumarK. Surf. Interfaces20233910291210.1016/j.surfin.2023.102912
    [Google Scholar]
  17. NazeriM.T. NasirianiT. FarhidH. JavanbakhtS. BahriF. ShadiM. ShaabaniA. 202210258115813410.1021/acssuschemeng.2c01030
  18. ImoisiliP.E. JenT.C. SafaeiB. Nanotechnol. Rev.202110112613610.1515/ntrev‑2021‑0016
    [Google Scholar]
  19. KostovaI. Molecules202429482410.3390/molecules29040824 38398576
    [Google Scholar]
  20. RahamanS.K. ChatterjeeT. AlamS.M. Synthesis of Metal-Organic Frameworks via Water.-Based Routes.Elsevier2024517210.1016/B978‑0‑323‑95939‑1.00009‑5
    [Google Scholar]
/content/journals/loc/10.2174/0115701786406873250730182802
Loading
/content/journals/loc/10.2174/0115701786406873250730182802
Loading

Data & Media loading...

Supplements

Supplementary material is available on the publisher's website along with the published article.

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test