Copper-incorporated fluorapatite encapsulated iron oxide nanocatalyst for synthesis of benzimidazoles
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
- Bansal and Silakari (2012) The therapeutic journey of benzimidazoles: a review (pp. 6208-6236) https://doi.org/10.1016/j.bmc.2012.09.013
- Ibrahim et al. (1980) Novel potential anticancer agents derived from benzimidazole (pp. 1348-1350) https://doi.org/10.1002/jps.2600691130
- Spasov et al. (2002) Pharmacokinetic of benzimidazole derivatives 48(3) (pp. 252-258)
- 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
- Santosh et al. (2011) Benzimidazole: a versatile chemical entity 2(6) (pp. 1126-1137)
- 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
- 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
- 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
- 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
- Wright (1951) The chemistry of the benzimidazoles (pp. 397-541) https://doi.org/10.1021/cr60151a002
- Ladenburg (1877) Condensationsvorgänge in der Orthoreihe Ber 10(1) (pp. 1123-1131)
- 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
- 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
- Khan et al. (2009) A simple and convenient one-pot synthesis of benzimidazole derivatives using cobalt(II) chloride hexahydrate as catalyst (pp. 2339-2346)
- 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
- 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
- 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
- Mohan et al. (2010) Microwave irradiation versus conventional method: synthesis of benzimidazolyl chalcone derivatives 2(3) (pp. 1634-1637)
- Tewari and Mishra (2006) Synthesis and antiviral activities of N-substituted-2-substituted-benzimidazole derivatives 45B(2006) (pp. 489-493)
- Perry and Wilson (1993) A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles 58(25) (pp. 7016-7021) https://doi.org/10.1021/jo00077a019
- Preston et al. (2008) Benzimidazoles and congeneric tricyclic compounds (pp. 6-60) Wiley
- 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
- Xiangming et al. (2007) p-TsOH catalyzed synthesis of 2-arylsubstituted benzimidazoles (pp. 150-154)
- 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
- 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
- Baars et al. (2014) Transition-metal-free synthesis of benzimidazoles mediated by KOH/DMSO (pp. 536-539) https://doi.org/10.1021/ol403414v
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
10.1007/s40097-017-0245-2