Skip to main content
Log in

Green synthesis of some 3-(α,α-diarylmethyl)indoles by bio-nanocomposite from embedding L–histidinium trichloroacetate ionic liquid on functionalized magnetite (L–His+CCl3CO2@PEG@SiO2–nano Fe3O4)

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

In this research, a new multilayered magnetized bio-nanocomposite has been prepared. At first, the amino acid-based ionic liquid was obtained from L-histidine and trichloroacetic acid (L–His+CCl3CO2), embedded on the polyethylene glycol-functionalized silicated-nanomagnetite, to prepare the final nanostructure (L–His+CCl3CO2@PEG@SiO2-nano Fe3O4). The bio-nanocomposite was characterized by several techniques such as FT-IR, FESEM, TGA/DTG, EDAX, TEM, VSM, and XRD. The catalytic activity of the core–shell nanostructure was examined in one-pot three-component reaction between aryl aldehydes, indoles, and β-naphthol/phenols to get some new 3-(α,α-diarylmethyl)indoles under solvent-free conditions at 75 °C. Eco-friendly protocol in the absence of hazardous solvents, no observation of by-products such as bis(indolyl)methanes (BIMs), in addition to recovery and reusability of the nanostructure within 3 runs without activity loss are some highlighted notable features of the work. The reused bio-nanocomposite was also characterized through FESEM technique.

Graphic abstract

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Scheme 3

Similar content being viewed by others

References

  1. Zhang Q, Lee I, Joo JB, Zaera F, Yin Y (2013) Core-shell nanostructured catalysts. Acc Chem Res 46:1816–1824. https://doi.org/10.1021/ar300230s

    Article  CAS  PubMed  Google Scholar 

  2. Chaudhuri RGh, Paria S (2012) Core/shell nanoparticles: classes, properties, synthesis mechanisms, characterization, and applications. Chem Rev 112:2373–2433. https://doi.org/10.1021/cr100449n

    Article  CAS  Google Scholar 

  3. Chen J, Ren Y, Li H, Yang W, Wu Q, Zhao Y, Jiao Q, Lu Y, Shi D (2020) Structural regulation of magnetic polymer microsphere@ionic liquids with an intermediate protective layer and application as core–shell–shell catalysts with high stability and activity. ACS Omega 5:23062–23069. https://doi.org/10.1021/acsomega.0c02777

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Chen J, Zhu X (2015) Ionic liquid coated magnetic core/shell Fe3O4@SiO2 nanoparticles for the separation/analysis of linuron in food samples. Spectrochim Acta A 137:456–462. https://doi.org/10.1016/j.saa.2014.08.113

    Article  CAS  Google Scholar 

  5. Xie W, Wang H (2020) Immobilized polymeric sulfonated ionic liquid on core-shell structured Fe3O4/SiO2 composites: a magnetically recyclable catalyst for simultaneous transesterification and esterifications of low-cost oils to biodiesel. Renew Energy 145:1709–1719. https://doi.org/10.1016/j.renene.2019.07.092

    Article  CAS  Google Scholar 

  6. Bahadorikhalili S, Ma’mani L, Mahdavi H, Shafiee A, (2015) Palladium catalyst supported on PEGylated imidazolium based phosphinite ionic liquid-modified magnetic silica core–shell nanoparticles: a worthy and highly water-dispersible catalyst for organic reactions in water. RSC Adv 5:71297–71305. https://doi.org/10.1039/C5RA12747E

    Article  CAS  Google Scholar 

  7. Mirhosseini-Eshkevari B, Esnaashari M, Ghasemzadeh MA (2019) Novel brönsted acidic ionic liquids confined in UiO-66 nanocages for the synthesis of dihydropyrido[2,3-d]pyrimidine derivatives under solvent-free conditions. ACS Omega 4:10548–10557. https://doi.org/10.1021/acsomega.9b00178

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Bodaghifard MA, Hamidinasab M, Ahadi N (2018) Recent advances in the preparation and application of organic-inorganic hybrid magnetic nanocatalysts on multicomponent reactions. Curr Org Chem 22:234–267. https://doi.org/10.2174/1385272821666170705144854

    Article  CAS  Google Scholar 

  9. Kazemi M, Mohammadi M (2020) Magnetically recoverable catalysts: catalysis in synthesis of polyhydroquinolines. Appl Organomet Chem 34:e5400. https://doi.org/10.1002/aoc.5400

    Article  CAS  Google Scholar 

  10. Payra S, Saha A, Banerjee S (2017) Recent advances on Fe-based magnetic nanoparticles in organic transformations. J Nanosci Nanotechnol 17:4432–4448. https://doi.org/10.1166/jnn.2017.14195

    Article  CAS  Google Scholar 

  11. Chen MN, Mo LP, Cui ZhSh, Zhang ZhH (2019) Magnetic nanocatalysts: synthesis and application in multicomponent reactions. Curr Opin Green Sustain Chem 15:27–37. https://doi.org/10.1016/j.cogsc.2018.08.009

    Article  Google Scholar 

  12. Munoz M, de Pedro ZM, Casas JA, Rodriguez JJ (2015) Preparation of magnetite-based catalysts and their application in heterogeneous Fenton oxidation–a review. Appl Catal B 176–177:249–265. https://doi.org/10.1016/j.apcatb.2015.04.003

    Article  CAS  Google Scholar 

  13. Sharma RK, Dutta S, Sharma Sh, Zboril R, Varma RS, Gawande MB (2016) Fe3O4 (iron oxide)-supported nanocatalysts: synthesis, characterization and applications in coupling reactions. Green Chem 18:3184–3209. https://doi.org/10.1039/C6GC00864J

    Article  CAS  Google Scholar 

  14. Shiri P, Aboonajmi J (2020) A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions. Beilstein J Org Chem 16:551–586. https://doi.org/10.3762/bjoc.16.52

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Ishikura M, Yamada K (2009) Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep 26:803–852. https://doi.org/10.1039/B820693G

    Article  CAS  PubMed  Google Scholar 

  16. Kumari A, Singh RK (2019) Medicinal chemistry of indole derivatives: current to future therapeutic prospectives. Bioorg Chem 89:103021. https://doi.org/10.1016/j.bioorg.2019.103021

    Article  CAS  PubMed  Google Scholar 

  17. Sravanthi TV, Manju SL (2016) Indoles-a promising scaffold for drug development. Eur J Pharm Sci 91:1–10. https://doi.org/10.1016/j.ejps.2016.05.025

    Article  CAS  PubMed  Google Scholar 

  18. Andreani A, Rambaldi M (1988) Indole derivatives as agrochemicals. J Heterocycl Chem 25:1519–1523. https://doi.org/10.1002/jhet.5570250549

    Article  CAS  Google Scholar 

  19. Rani P, Srivastava VK, Kumar A (2004) Synthesis and antiinflammatory activity of heterocyclic indole derivatives. Eur J Med Chem 39:449–452. https://doi.org/10.1016/j.ejmech.2003.11.002

    Article  CAS  PubMed  Google Scholar 

  20. Grumel V, Me´rour JY, Lesur B, Giboulot Th, Frydman A, Guillaumet G (2002) Design and synthesis of a series of indole glycoprotein IIb/IIIa inhibitors. Eur J Med Chem 37:45–62. https://doi.org/10.1016/S0223-5234(01)01325-3

    Article  CAS  PubMed  Google Scholar 

  21. Reddy BVS, Reddy MR, Madan Ch, Kumar KP, Rao MS (2010) Indium(III) chloride catalyzed three-component coupling reaction: a novel synthesis of 2-substituted aryl(indolyl)kojic acid derivatives as potent antifungal and antibacterial agents. Bioorg Med Chem Lett 20:7507–7511. https://doi.org/10.1016/j.bmcl.2010.10.003

    Article  CAS  PubMed  Google Scholar 

  22. Nikoofar K, Peyrovebaghi SS (2020) Ultrasound-assisted synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones by novel core-shell bio-based nanocatalyst anchoring sulfonated L-histidine on magnetized silica (SO3H-L-His@SiO2-nano Fe3O4). J Chin Chem Soc 67:1303–1313. https://doi.org/10.1002/jccs.201900365

    Article  CAS  Google Scholar 

  23. Molaei Yielzoleh F, Nikoofar K (2021) Magnetized inorganic-bioorganic nanohybrid [nano Fe3O4-SiO2@Glu-Cu (II)]: a novel nanostructure for the efficient solvent-free synthesis of thiazolidin-2-imines. Appl Organomet Chem 35:e6043. https://doi.org/10.1002/aoc.6043

    Article  CAS  Google Scholar 

  24. Nikoofar K, Moazzez Dizgarani Sh (2019) p-TSA@nano SiO2 as a new and efficient nanocatalyst for the one-pot multi-component synthesis of some novel 1-amidoalkyl-2-naphthols under solvent-free conditions. Proc Natl Acad Sci India A 89:629–641. https://doi.org/10.1007/s40010-018-0531-5

    Article  CAS  Google Scholar 

  25. Molaei Yielzoleh F, Nikoofar K (2021) Novel inorganic-bioorganic functionalized silica-magnetized core-shell (nano SO3H-D-Leu@SiO2-Fe3O4) as reusable promoter for the synthesis of 7,7’-((aryl)methylene)bis(N-cyclohexyl-2-(aryl)-6-methyl-3H-imidazo[1,2-b]pyrazol-3-imine) derivatives. Polycycl Aromat Compd. https://doi.org/10.1080/10406638.2021.1878248

    Article  Google Scholar 

  26. Nikoofar K, Mehrikaram F (2019) Graphite decorated nano alumina (nano Al2O3@Cg): a versatile inorganic nano-promoter for the synthesis of 4-alkyl-5-methyl-1H-pyrazol-3-ols in aqueous media. Polyhedron 159:330–336. https://doi.org/10.1016/j.poly.2018.12.008

    Article  CAS  Google Scholar 

  27. Nikoofar K, Heidari H, Shahedi Y (2018) Nano crystalline cellulose sulfuric acid (s-NCC): a novel green nanocatalyst for the synthesis of polyhydroxy pyrimidine-fused heterocyclic compounds (PPFHs). Cellulose 25:5697–5709. https://doi.org/10.1007/s10570-018-1942-9

    Article  CAS  Google Scholar 

  28. Deb ML, Borpatra PJ, Saikia PJ, Baruah PK (2017) Base-promoted three-component one-pot approach to 3-(α, α-diarylmethyl) indoles via arylation of 3-indolylalcohols. Synthesis 49:1401–1409. https://doi.org/10.1055/s-0036-15880098

    Article  CAS  Google Scholar 

  29. Borpatra PJ, Deka B, Rajbongshi BK, Deb ML, Baruah PK (2018) One-pot sequential multi-component reaction: synthesis of 3-substituted indoles. Synth Commun 48:2074–2082. https://doi.org/10.1080/00397911.2018.1482352

    Article  CAS  Google Scholar 

  30. Cid R, Pecchi G (1985) Potentiometric method for determining the number and relative strength of acid sites in colored catalysts. Appl Catal 14:15–21. https://doi.org/10.1016/S0166-9834(00)84340-7

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors appreciate Alzahra University for financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kobra Nikoofar.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 4133 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikoofar, K., Saheb Ekhtiari, N. Green synthesis of some 3-(α,α-diarylmethyl)indoles by bio-nanocomposite from embedding L–histidinium trichloroacetate ionic liquid on functionalized magnetite (L–His+CCl3CO2@PEG@SiO2–nano Fe3O4). Mol Divers 26, 1425–1439 (2022). https://doi.org/10.1007/s11030-021-10268-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-021-10268-6

Keywords

Navigation