10.1007/s40097-017-0245-2

Copper-incorporated fluorapatite encapsulated iron oxide nanocatalyst for synthesis of benzimidazoles

  1. Department of Chemistry, University of Guilan, Rasht, IR
  2. Department of Chemistry, Faculty of Sciences, University of Guilan, Rasht, IR
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Published in Issue 07-11-2017

How to Cite

Mirfarjood, S. A., Mamaghani, M., & Sheykhan, M. (2017). Copper-incorporated fluorapatite encapsulated iron oxide nanocatalyst for synthesis of benzimidazoles. Journal of Nanostructure in Chemistry, 7(4 (December 2017). https://doi.org/10.1007/s40097-017-0245-2

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Abstract

Abstract γ-Fe 2 O 3 @CuFAp nanocatalyst was synthesized and characterized by several methods including XRD, SEM, TEM, ICP, and FT-IR analyses. The γ-Fe 2 O 3 @CuFAp has been used as an efficient recyclable magnetic catalyst for synthesis of benzimidazoles. The γ-Fe 2 O 3 @CuFAp was conveniently separated from the reaction mixture by an external magnet, and could be reused at least 12 times without any considerable change in catalytic activity. Graphical abstract

Keywords

  • Nanocatalyst,
  • γ-Fe2O3@CuFAp,
  • Benzimidazole

References

  1. Bansal and Silakari (2012) The therapeutic journey of benzimidazoles: a review (pp. 6208-6236) https://doi.org/10.1016/j.bmc.2012.09.013
  2. Ibrahim et al. (1980) Novel potential anticancer agents derived from benzimidazole (pp. 1348-1350) https://doi.org/10.1002/jps.2600691130
  3. Spasov et al. (2002) Pharmacokinetic of benzimidazole derivatives 48(3) (pp. 252-258)
  4. Janssens et al. (1985) New antihistaminic N-heterocyclic 4-piperidinamines. 1. Synthesis and antihistaminic activity of N-(4-piperidinyl)-1H-benzimidazol-2-amines 28(12) (pp. 1925-1933) https://doi.org/10.1021/jm00150a028
  5. Santosh et al. (2011) Benzimidazole: a versatile chemical entity 2(6) (pp. 1126-1137)
  6. Ozden et al. (2005) Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups (pp. 1587-1597) https://doi.org/10.1016/j.bmc.2004.12.025
  7. Chen et al. (2012) Synthesis and anti-inflammatory evaluation of novel benzimidazole and imidazopyridine derivatives 4(1) (pp. 69-74) https://doi.org/10.1021/ml300282t
  8. Shingalapur et al. (2010) Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies (pp. 1753-1759) https://doi.org/10.1016/j.ejmech.2010.01.007
  9. Mathew et al. (2016) Development of novel (1-H) benzimidazole bearing pyrimidine-trione based MAO-A inhibitors: synthesis, docking studies and antidepressant activity (pp. S132-S139) https://doi.org/10.1016/j.jscs.2012.09.015
  10. Wright (1951) The chemistry of the benzimidazoles (pp. 397-541) https://doi.org/10.1021/cr60151a002
  11. Ladenburg (1877) Condensationsvorgänge in der Orthoreihe Ber 10(1) (pp. 1123-1131)
  12. Neef et al. (1981) One-step conversions of esters to 2-imidazolines, benzimidazoles and benzothiazoles by aluminum organic reagents (pp. 2824-2826) https://doi.org/10.1021/jo00326a055
  13. Singh et al. (2000) Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: a facile access to substituted benzimidazole, bisbenzimidazole and imidazopyridine derivatives (pp. 1380-1390) https://doi.org/10.1055/s-2000-7111
  14. Khan et al. (2009) A simple and convenient one-pot synthesis of benzimidazole derivatives using cobalt(II) chloride hexahydrate as catalyst (pp. 2339-2346)
  15. Gogoi and Konwar (2006) An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water 47(1) (pp. 79-82) https://doi.org/10.1016/j.tetlet.2005.10.134
  16. Chakrabarty et al. (2009) A mild and expedient one-pot synthesis of substituted benzimidazoles in water using a phase-transfer catalyst 140(4) (pp. 375-380) https://doi.org/10.1007/s00706-008-0036-z
  17. Yadagiri and Lown (1990) Convenient routes to substituted benzimidazoles and imidazolo [4, 5-b] pyridines using nitrobenzene as oxidant 20(7) (pp. 955-963) https://doi.org/10.1080/00397919008052798
  18. Mohan et al. (2010) Microwave irradiation versus conventional method: synthesis of benzimidazolyl chalcone derivatives 2(3) (pp. 1634-1637)
  19. Tewari and Mishra (2006) Synthesis and antiviral activities of N-substituted-2-substituted-benzimidazole derivatives 45B(2006) (pp. 489-493)
  20. Perry and Wilson (1993) A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles 58(25) (pp. 7016-7021) https://doi.org/10.1021/jo00077a019
  21. Preston et al. (2008) Benzimidazoles and congeneric tricyclic compounds (pp. 6-60) Wiley
  22. Ma et al. (2007) Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles promoted by Ionic liquid (pp. 135-140) https://doi.org/10.3987/COM-06-10920
  23. Xiangming et al. (2007) p-TsOH catalyzed synthesis of 2-arylsubstituted benzimidazoles (pp. 150-154)
  24. Ben-Alloum et al. (1998) Benzimidazoles: oxydation heterocyclisante par le nitrobenzene ou le dimethylsulfoxyde sur silice et sous irradiation micro-ondes ou ultra-violet 39(25) (pp. 4481-4484) https://doi.org/10.1016/S0040-4039(98)00868-5
  25. Lu et al. (2002) Microwave irradiation synthesis of 2-substituted benzimidazoles using PPA as a catalyst under solvent-free conditions 32(24) (pp. 3703-3709) https://doi.org/10.1081/SCC-120015381
  26. Baars et al. (2014) Transition-metal-free synthesis of benzimidazoles mediated by KOH/DMSO (pp. 536-539) https://doi.org/10.1021/ol403414v
  27. Massart et al. (1995) Preparation and properties of monodisperse magnetic fluids 149(1–2) (pp. 1-5) https://doi.org/10.1016/0304-8853(95)00316-9
  28. Tang et al. (1999) Processible nanostructured materials with electrical conductivity and magnetic susceptibility: preparation and properties of maghemite/polyaniline nanocomposite films 11(6) (pp. 1581-1589) https://doi.org/10.1021/cm9900305
  29. Ho and Li (2008) Design and synthesis of novel magnetic core–shell polymeric particles 24(5) (pp. 1801-1807) https://doi.org/10.1021/la702887m
  30. Mirfarjood et al. (2017) Copper-exchanged magnetic-FAp: surface catalysis in decarboxylative coupling of a-oxocarboxylic acids with formamides (pp. 8650-8657) https://doi.org/10.1002/slct.201701438
  31. Soleimani et al. (2015) Synthesis of 2-substituted benzimidazoles and benzothiazoles using Ag2CO3/Celite as an efficient solid catalyst 12(7) (pp. 1281-1285) https://doi.org/10.1007/s13738-015-0592-1
  32. Forouzani and Ghasemnejad-Bosra (2012) 1,3-Dibromo 5, 5-dimethylhydantoin (DBH)-catalyzed solvent-Free synthesis of 2-arylbenzimidazoles under microwave irradiation 9(3) (pp. 1064-1069) https://doi.org/10.1155/2012/454213
  33. Shen and Driver (2008) Iron (II) bromide-catalyzed synthesis of benzimidazoles from aryl azides 10(15) (pp. 3367-3370) https://doi.org/10.1021/ol801227f
  34. Yu et al. (2014) Iron-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles, benzoxazoles, and benzothiazoles directly from aromatic primary amines under solvent-free conditions in the open air 44(20) (pp. 3019-3026) https://doi.org/10.1080/00397911.2014.914221
  35. Brătulescu (2017) Mild, one-pot preparation of 2-substituted benzimidazoles from organic halides 47(8) (pp. 811-817) https://doi.org/10.1080/00397911.2017.1287922
  36. Shen and Cai (2007) Ytterbium perfluorooctanesulfonates catalyzed synthesis of benzimidazole derivatives in fluorous solvents 128(3) (pp. 232-235) https://doi.org/10.1016/j.jfluchem.2007.01.009
  37. Alvim et al. (2015) Synthesis of 2-arylbenzimidazoles under mild conditions catalyzed by a heteropolyacid-containing task-specific ionic liquid and catalyst investigation by electrospray (tandem) mass spectrometry 5(88) (pp. 69418-69422) https://doi.org/10.1039/C5RA12044F
  38. Sharghi et al. (2008) Reusable porphyrinatoiron(III) complex supported on activated silica as an efficient heterogeneous catalyst for a facile, one-pot, selective synthesis of 2-arylbenzimidazole derivatives in the presence of atmospheric air as a “green” oxidant at ambient temperature 2008(24) (pp. 4126-4138) https://doi.org/10.1002/ejoc.200800351
  39. Behbahani et al. (2014) Synthesis of 2-substituted benzimidazoles using 25% Co/Ce-ZrO2 as a heterogeneous and nanocatalyst 144(12) (pp. 2184-2190) https://doi.org/10.1007/s10562-014-1372-8