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. 2018 Aug 2;8(49):27631-27644.
doi: 10.1039/c8ra04368j.

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

Mahmoud Nasrollahzadeh  1 , Zahra Issaabadi  1 , S Mohammad Sajadi  2
Affiliations

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

Mahmoud Nasrollahzadeh et al. RSC Adv. .

Abstract

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Brønsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of 1-carbamoyl-1-phenylureas.
Scheme 2
Scheme 2. Preparation of arylcyanamides (A) and 5-phenyl-1H-tetrazole (B).
Scheme 3
Scheme 3. Synthesis of {Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole-SO3H/Cl}.
Fig. 1
Fig. 1. The EDS spectra of Fe3O4@SiO2 (A), Fe3O4@SiO2@(CH2)3-Cl (B), Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole (C) and [FSTet-SO3H]Cl (D).
Fig. 2
Fig. 2. FESEM images of Fe3O4@SiO2 (A), Fe3O4@SiO2@(CH2)3Cl (B), Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole (C) and [FSTet-SO3H]Cl (D).
Fig. 3
Fig. 3. TEM images of [FSTet-SO3H]Cl.
Fig. 4
Fig. 4. TG-DTA analysis of [FSTet-SO3H]Cl.
Fig. 5
Fig. 5. The FT-IR spectra of 5-phenyl-1H-tetrazole (A), Fe3O4@SiO2 (B), Fe3O4@SiO2@(CH2)3Cl (C), Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole (D) and [FSTet-SO3H]Cl (E).
Fig. 6
Fig. 6. The XRD patterns of Fe3O4@SiO2 (A), Fe3O4@SiO2@(CH2)3Cl (B), Fe3O4@SiO2@(CH2)35-phenyl-1H-tetrazole (C) and [FSTet-SO3H]Cl (D).
Fig. 7
Fig. 7. Magnetization curve for [FSTet-SO3H]Cl.
Scheme 4
Scheme 4. Preparation of primary carbamates.
Fig. 8
Fig. 8. FT-IR spectrum of 1-carbamoyl-1-(3-bromophenyl)urea (1).
Fig. 9
Fig. 9. Expanded 1H NMR spectrum (400 MHz, CDCl3) of 1-carbamoyl-1-(3-bromophenyl)urea (1).
Fig. 10
Fig. 10. 13C NMR spectrum (100 MHz, CDCl3) of 1-carbamoyl-1-(3-bromophenyl)urea (1).
Scheme 5
Scheme 5. Possible mechanism for the synthesis of 1-carbamoyl-1-phenylureas.
Fig. 11
Fig. 11. Chemical structures of many bioactive arylureas.
Fig. 12
Fig. 12. Antibacterial activity of 2-(4-(1-carbamoylureido)phenyl)malonamide (7) against E. coli.
Fig. 13
Fig. 13. Reusability of [FSTet-SO3H]Cl for the synthesis of 1-carbamoyl-1-(4-methoxylphenyl)urea.
Fig. 14
Fig. 14. FESEM images of recovered [FSTet-SO3H]Cl.
Fig. 15
Fig. 15. TEM images of recovered [FSTet-SO3H]Cl.
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References

    1. Marsh K. N. Boxall J. A. Lichtenthaler R. Fluid Phase Equilib. 2004;219:93. doi: 10.1016/j.fluid.2004.02.003. - DOI
    1. Bentivoglio G. Röder T. Fasching M. Buchberger M. Schottenberger H. Sixta H. Lenzinger Ber. 2006;86:154.
    1. Welton T. Chem. Rev. 1999;99(8):2071. doi: 10.1021/cr980032t. - DOI - PubMed
    2. Yue C. Fang D. Liu L. Yi T. F. J. Mol. Liq. 2011;163:99. doi: 10.1016/j.molliq.2011.09.001. - DOI
    3. Greaves T. L. Drummond C. J. Chem. Rev. 2008;108:206. doi: 10.1021/cr068040u. - DOI - PubMed
    4. Hallett J. P. Welton T. Chem. Rev. 2011;111:3508. doi: 10.1021/cr1003248. - DOI - PubMed
    1. Jonathan G. H. Heather D. W. Richard P. S. Ann E. V. Robin D. R. Chem. Commun. 1998;16:1765.
    1. Pham T. P. T. Cho C. W. Yun Y. S. Water Res. 2010;44:352. doi: 10.1016/j.watres.2009.09.030. - DOI - PubMed