Skip to main content
SpringerLink
Log in

Magnetically recoverable nano Pd/Fe3O4/ZnO catalyst: preparation, characterization, and application for the synthesis of 2-oxazolines and benzoxazoles

  • Original Paper
  • Published:
Journal of Materials Science Aims and scope Submit manuscript

Abstract

A novel palladium-based catalysts supported on Fe3O4/ZnO nanoparticles have been prepared by a simple method. The catalyst was characterized by transmission electron microscopy, X-ray powder diffraction, X-ray photoelectron spectroscopy, atomic absorption spectrophotometry, FT-IR, and BET analysis. The catalyst afforded efficient synthesis of 2-oxazolines and benzoxazoles from aromatic nitriles under solvent-free conditions. The significant features of this method are short reaction times, good to high yields of the products, simple operation, solvent-free condition, non-toxicity, reusability of the catalyst without significant loss of catalytic activity, and using ultra small amount of Pd (0.004 g of catalyst contains 9.16 × 10−3 mmol Pd which was determined by ICP).

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

Similar content being viewed by others

References

  1. Evindar G, Batey RA (2006) Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides. J Org Chem 71:1802–1808

    Article  Google Scholar 

  2. Wipf P (1998) In: Pelletier SW (ed) Alkaloids: chemical and biological perspectives, Pergamon: New York, p 187–228

  3. Easmon J, Pürstinger G, Thies K-S, Heinisch G, Hofmann J (2006) Synthesis, structure–activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics. J Med Chem 49:6343–6350

    Article  Google Scholar 

  4. Grobler JA, Dornadula G, Rice MR, Simcoe AL, Hazuda DJ, Miller MD (2007) Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by silica sulfuric acid. J Biol Chem 282:8005–8010

    Article  Google Scholar 

  5. Leventhal L, Brandt MR, Cummons TA, Piesla MJ, Rogers KE, Harris HA (2006) An estrogen receptor-beta agonist is active in models of inflammatory and chemical-induced pain. Eur J Pharmacol 553:146–148

    Article  Google Scholar 

  6. Sha C-K, Huang S-J, Zhan Z-P (2002) Anionic cyclization approach toward perhydrobenzofuranone: stereocontrolled synthesis of the hexahydrobenzofuran subunit of avermectin. J Org Chem 67:831–834

    Article  Google Scholar 

  7. Witte H, Seeliger W (1974) Cyclische imidsäureester aus nitrilen und aminoalkoholen. Liebigs Ann Chem 1974:996–1009

    Article  Google Scholar 

  8. Zhang D-X, Xiang S–K, Hu H, Tan W, Feng C, Wang B-Q, Zhao K-Q, Zhao K-Q, Hu P, Yang H (2013) An improved protocol for synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles. Tetrahedron 69:10022–10029

    Article  Google Scholar 

  9. Lester RP, Camp JE (2013) Methods for the direct synthesis of benzoxazoles from halogenated nitriles in alcoholic solvents, ACS Sustainable. Chem Eng 1:545–548

    Google Scholar 

  10. Heng T, Xu Y-L, Pan C-x, Wang H-s, Pan Y-m (2012) Synthesis of benzoxazoles by the copper triflate catalysed reaction of nitriles and o-aminophenols. J Chem Res 3:370–373

    Google Scholar 

  11. Holljes EL, Wagner EC (1944) Some reactions of nitriles as acid anammonides. J Org Chem 9:31–49

    Article  Google Scholar 

  12. Xiang S-K, Zhang D-X, Hu H, Shi J-L, Liao L-G, Feng C, Wang B-Q, Zhao K-Q, Hu P, Yang H, Yu W-H (2013) Synthesis of n-arylamides by copper-catalyzed amination of aryl halides with nitriles. Adv Synth Catal 355:1495–1499

    Article  Google Scholar 

  13. Whelligan DK, Bolm C (2006) The synthesis of pseudo-geminal, pseudo-ortho and ortho phosphinyl-oxazolinyl-[2.2]paracyclophanes for use as ligands in asymmetric catalysis. J Org Chem 71:4609–4618

    Article  Google Scholar 

  14. Kangani CO, Kelley DE, Day BW (2006) One pot direct synthesis of oxazolines, benzoxazoles, and oxadiazoles from carboxylic acids using the deoxo-fluor reagent. Tetrahedron Lett 47:6497–6499

    Article  Google Scholar 

  15. Wen X, Bakali J, Deprez-Poulain R, Deprez B (2012) Efficient propylphosphonic anhydride (®T3P) mediated synthesis of benzothiazoles, benzoxazoles and benzimidazoles. Tetrahedron Lett 53:2440–2443

    Article  Google Scholar 

  16. Hughey JL, Knapp S, Schugar H (1980) Dehydrogenation of 2-imidazolines to imidazoles with barium manganate. Synthesis 1980:489–490

    Article  Google Scholar 

  17. Aidouni A, Demonceau A, Delaude L (2006) Microwave-assisted synthesis of n-heterocyclic carbene precursors. Synlett 3:493–495

    Google Scholar 

  18. Katritzky AR, Cai CM, Suzuki K, Singh SK (2004) Facile syntheses of oxazolines and thiazolines with N-acylbenzotriazoles under microwave irradiation. J Org Chem 69:811–814

    Article  Google Scholar 

  19. Bastug G, Eviolitte C, Markó IE (2012) Functionalized orthoesters as powerful building blocks for the efficient preparation of heteroaromatic bicycles. Org Lett 14:3502–3505

    Article  Google Scholar 

  20. Suresh D, Dhakshinamoorthy A, Pitchumani K (2013) A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay. Tetrahedron Lett 54:415–6419

    Google Scholar 

  21. Shelkar R, Sarode S, Nagarkar J (2013) Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media. Tetrahedron Lett 54:6986–6990

    Article  Google Scholar 

  22. Prasad AS, Bollikonda S (2012) Synthesis of aryl 2-oxazolines from aromatic nitriles and aminoalcohols using magnetically recoverable Pd/Fe3O4. Der Pharm Chem 4:93–99

    Google Scholar 

  23. Polshettiwar V, Varma RS (2009) Nanoparticle-supported and magnetically recoverable ruthenium hydroxide catalyst: efficient hydration of nitriles to amides in aqueous medium. Chem Eur J 15:1582–1586

    Article  Google Scholar 

  24. Le Goff A, Artero V, Jousselme B, Tran PD, Guillet N, Métayé R, Fihri A, Palacin S, Fontecave M (2009) From hydrogenases to noble metal–free catalytic nanomaterials for h2 production and uptake. Science 326:1384–1387

    Article  Google Scholar 

  25. Berseth PA, Harter AG, Zidan R, Blomqvist A, Araujo CM, Scheicher RH, Ahuja R, Jena P (2009) Carbon nanomaterials as catalysts for hydrogen uptake and release in NaAlH4. Nano Lett 9:1501–1505

    Article  Google Scholar 

  26. Nadagouda MN, Polshettiwar V, Varma RS (2010) Self-assembly of palladium nanoparticles: synthesis of nanobelts, nanoplates and nanotrees using vitamin B1, and their application in carbon–carbon coupling reactions. J Mater Chem 19:2026–2031

    Article  Google Scholar 

  27. Polshettiwar V, Varma RS (2010) Green chemistry by nano-catalysis. Green Chem 12:743–754

    Article  Google Scholar 

  28. Hosseini-Sarvari M (2013) Catalytic organic reactions on ZnO. Curr Org Synth 10(5):697–723

    Article  Google Scholar 

  29. Hosseini-Sarvari M, Roosta A (2014) Synthesis of 2-amino-4H-chromen-4-yl phosphonats via C–P bond formation catalyzed by nano-rods ZnO under solvent-free condition. Comb Chem High T Screen 1:47–52

    Article  Google Scholar 

  30. Hosseini-Sarvari M, Moeini F (2014) Nano copper(I) oxide/zinc oxide catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides and arylboronic acids in air. RSC Adv 4:7321–7329

    Article  Google Scholar 

  31. Cao J, Fu W, Yang H, Yu Q, Zhang Y, Wang S, Zhao H, Sui Y, Zhou X, Zhao W, Leng Y, Zhao H, Chen H, Qi X (2010) Fabrication, characterization and application in electromagnetic wave absorption of flower-like ZnO/Fe3O4 nanocomposites. Mat Sci Eng B 175:56–59

    Article  Google Scholar 

  32. Ge H, Liu P, Li X, Sun W, Li J, Yang B, Shi Z (2013) S–Co(II) cascade catalysis: cyclocondensation of aromatic nitriles with alkamine. Tetrahedron 69:6591–6597

    Article  Google Scholar 

  33. Teimouria A, Najafi Chermahinib A, Salavatia H, Ghorbanianc L (2013) An efficient and one-pot synthesis of benzimidazoles, benzoxazoles, benzothiazoles and quinoxalines catalyzed via nano-solid acid catalysts. J Mol Catal A Chem 373:38–45

    Article  Google Scholar 

  34. Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Kargar H (2009) InCl3 as an efficient catalyst for synthesis of oxazolines under thermal, ultrasonic and microwave irradiations. J Iran Chem Soc 2:251–258

    Article  Google Scholar 

  35. Xu Q, Li Z (2009) A facile synthesis of 2-oxazolines using a PPh3-DDQ system. Tetrahedron Lett 50:6838–6840

    Article  Google Scholar 

  36. Boissarie PJ, Hamilton ZE, Lang S, Murphy JA, Suckling CJ (2011) A powerful palladium-catalyzed multicomponent process for the preparation of oxazolines and benzoxazoles. Org Lett 13:6256–6259

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the support of this work by the Shiraz University. We are also grateful to Mr. H. Sajedian Fard for helpful cooperation.

Author information

Authors and Affiliations

  1. Department of Chemistry, Shiraz University, 71454, Shiraz, Islamic Republic of Iran

    Mona Hosseini-Sarvari, Ameneh Khanivar & Fatemeh Moeini

Authors
  1. Mona Hosseini-Sarvari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ameneh Khanivar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fatemeh Moeini
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mona Hosseini-Sarvari.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hosseini-Sarvari, M., Khanivar, A. & Moeini, F. Magnetically recoverable nano Pd/Fe3O4/ZnO catalyst: preparation, characterization, and application for the synthesis of 2-oxazolines and benzoxazoles. J Mater Sci 50, 3065–3074 (2015). https://doi.org/10.1007/s10853-015-8866-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-015-8866-7

Keywords

Search

Navigation