Nanomagnetic macrocyclic Schiff-base-Mn(ii) complex: an efficient heterogeneous catalyst for click approach synthesis of novel β-substitued-1,2,3-triazoles.

Saade Abdalkareem Jasim, Yassine Riadi, Hasan Sh Majdi, Usama S Altimari
Author Information
  1. Saade Abdalkareem Jasim: Medical Laboratory Techniques Department, Al-Maarif University College Al-Anbar-Ramadi Iraq.
  2. Yassine Riadi: Department of Pharmaceutics, College of Pharmacy, Prince Sattam Bin Abdulaziz University Al-Kharj 11942 Saudi Arabia yassine.riadi2022@gmail.com y.riadi2@psau.edu.sa. ORCID
  3. Hasan Sh Majdi: Department Chemical Engineering and Petroleum Industries, Al-Mustaqbal University College 51001 Iraq.
  4. Usama S Altimari: Department of Pharmaceutics, Al-Nisour University College Baghdad Iraq.

Abstract

In the present work, a novel symmetrical 15-membered macrocyclic Schiff base complex of manganese was prepared using the reaction of the synthetic 2,6-diacetylpyridine functionalized FeO MNPs with 2,2-(piperazine-1,4-diyl)dianiline and Mn(ii) bromide salt a template approach. The resulting [FeO@PAM-Schiff-base-Mn][ClO] heterogenized complex was characterized using FT-IR, XRD, BET, TGA, EDX, Xray-mapping, SEM, TEM and VSM analysis. To demonstrate proof of concept, Huisgen 1,3-dipolar cycloaddition synthesis of 1,2,3-triazoles was selected to evaluate the activity and reusability of the catalyst. The ethanol as a green solvent proved to be an excellent reaction medium for this synthesis. Yields of up to 100% were obtained in some cases. Significantly, as demonstrated, [FeO@PAM-Schiff-base-Mn][ClO] catalyst was recycled for 8 cycles without losing catalytic activity under the optimized reaction conditions. The hot filtration and ICP-OES tests ratified that there was no leaching of metal during the catalytic reaction, indicating the heterogeneous manner of the catalyst.

References

  1. Curr Org Synth. 2019;16(6):855-899 [PMID: 31984910]
  2. Molecules. 2021 May 28;26(11): [PMID: 34071629]
  3. J Environ Manage. 2021 Feb 1;279:111603 [PMID: 33172705]
  4. Curr Org Synth. 2021;18(2):101-124 [PMID: 32928090]
  5. Chem Rev. 2022 May 11;122(9):8594-8757 [PMID: 35240777]
  6. Chem Rec. 2021 Oct;21(10):2762-2781 [PMID: 33538117]
  7. Molecules. 2021 May 06;26(9): [PMID: 34066456]
  8. Mater Sci Eng C Mater Biol Appl. 2016 Sep 1;66:106-118 [PMID: 27207044]
  9. J Org Chem. 2011 Oct 21;76(20):8394-405 [PMID: 21894972]
  10. Angew Chem Int Ed Engl. 2010 May 3;49(20):3428-59 [PMID: 20419718]
  11. ACS Comb Sci. 2011 Mar 14;13(2):135-9 [PMID: 21218828]
  12. Angew Chem Int Ed Engl. 2020 Jul 20;59(30):12293-12307 [PMID: 32255543]
  13. Sci Rep. 2022 Mar 8;12(1):3771 [PMID: 35260647]
  14. Bioorg Chem. 2021 Oct;115:105184 [PMID: 34333421]
  15. Photochem Photobiol Sci. 2009 Nov;8(11):1499-516 [PMID: 19862408]
  16. Pharmaceutics. 2020 Aug 02;12(8): [PMID: 32748814]
  17. Chem Rev. 2019 Sep 11;119(17):9836-9860 [PMID: 30990310]
  18. RSC Adv. 2020 Apr 20;10(26):15461-15492 [PMID: 35558641]
  19. Chem Rev. 2022 Feb 9;122(3):3637-3710 [PMID: 34910451]
  20. ACS Omega. 2020 Oct 14;5(42):27119-27132 [PMID: 33134672]
  21. Bioorg Med Chem Lett. 2018 Apr 1;28(6):1005-1010 [PMID: 29486969]
  22. J Org Chem. 2019 Sep 20;84(18):11971-11982 [PMID: 31464125]
  23. Sci Rep. 2022 Feb 21;12(1):2867 [PMID: 35190576]
  24. Sci Rep. 2016 Sep 21;6:33659 [PMID: 27651005]
  25. Steroids. 2020 Feb;154:108548 [PMID: 31805293]
  26. Chem Rev. 2017 Feb 22;117(4):2730-2784 [PMID: 27779851]
  27. Molecules. 2021 Dec 30;27(1): [PMID: 35011463]
  28. Org Lett. 2018 Jun 15;20(12):3460-3464 [PMID: 29809014]
  29. Carbohydr Polym. 2021 Dec 1;273:118619 [PMID: 34561015]
  30. RSC Adv. 2021 Mar 31;11(21):12614-12625 [PMID: 35423821]
  31. ACS Omega. 2019 Sep 16;4(14):16016-16025 [PMID: 31592125]
  32. Chem Asian J. 2020 Oct 1;15(19):2960-2983 [PMID: 32706483]
  33. Molecules. 2022 Mar 19;27(6): [PMID: 35335350]
  34. Int J Nanomedicine. 2022 Feb 08;17:589-601 [PMID: 35173432]
  35. RSC Adv. 2018 Jan 22;8(7):3889-3898 [PMID: 35542945]
  36. Tetrahedron. 2011 Oct 28;67(43):8213-8228 [PMID: 32287421]

Word Cloud

Created with Highcharts 10.0.0reaction2catalystsynthesisnovelmacrocycliccomplexusingiiapproach[FeO@PAM-Schiff-base-Mn][ClO]13-triazolesactivitycatalyticheterogeneouspresentworksymmetrical15-memberedSchiffbasemanganesepreparedsynthetic6-diacetylpyridinefunctionalizedFeOMNPs2-piperazine-14-diyldianilineMnbromidesalttemplateresultingheterogenizedcharacterizedFT-IRXRDBETTGAEDXXray-mappingSEMTEMVSManalysisdemonstrateproofconceptHuisgen3-dipolarcycloadditionselectedevaluatereusabilityethanolgreensolventprovedexcellentmediumYields100%obtainedcasesSignificantlydemonstratedrecycled8cycleswithoutlosingoptimizedconditionshotfiltrationICP-OEStestsratifiedleachingmetalindicatingmannerNanomagneticSchiff-base-Mncomplex:efficientclickβ-substitued-1

Similar Articles

Cited By (2)