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Current Organic Synthesis

Author(s): Vajihe Nejadshafiee and Hossein Naeimi*

DOI: 10.2174/1570179415666181031123504

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Molecular Ionic Liquid Supported on Mesoporous Silica Nanoparticles-Imprinted Iron Metal: A Recyclable Heterogeneous Catalyst for One-Pot, Three-Component Synthesis of a Library of Benzodiazepines

Page: [136 - 144] Pages: 9

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Abstract

Aim and Objective: A novel and convenient transformation for the synthesis of benzodiazepines has been developed via catalytic cyclization reaction using ionic liquid supported on mesoporous silica nanoparticles- imprinted iron metal (Fe-MCM-41-IL) as a recyclable catalyst under mild conditions.

Materials and Methods: For preparation of Fe-MCM-41-IL, FeCl3·6H2O was added to a mixture of distilled water, CTAB and NaOH aqueous solution. The tetraethyl orthosilicate was dropped into the solution under stirring. The product was separated, washed, and dried. The solid product was collected and calcined. Then, to a solution of β-hydroxy-1,2,3-triazole in toluene, 3-chloropropyltrimethoxysilane was added and the mixture was refluxed. The Conc. H2SO4 was added dropwise into the above solution and stirred. For immobilization of IL onto Fe-MCM-41, the solution IL was added to Fe-MCM-41 and was refluxed for the production of the Fe- MCM-41. Following this, benzodiazepines were synthesized using Fe-MCM-41-IL as a catalyst.

Results: The Fe-MCM-41-IL was prepared and characterized by a different analysis. The activity of the prepared catalyst as the above described was tested in the model reaction of o-phenyldiamine, tetronic acid, and different aldehydes under room temperature in ethanol solvent. Also, the catalyst could be recovered for five cycles.

Conclusion: We developed a novel nanocatalyst for the synthesis of benzodiazepines in excellent yields. Fe- MCM-41-IL as a catalyst has advantages such as: environmental friendliness, reusability and easy recovery of the catalyst using an external magnet.

Keywords: Ionic liquid, mesoporous, Fe-MCM-41-IL, nanocatalyst, benzodiazepines, synthesis.

Graphical Abstract

[1]
Schutz, H. Benzodiazepines; Springer: Heidelberg, 1982.
[2]
Landquist, J.K.; Katritzky, A.R.; Rees, C.W. Pergamon In: Comprehensive Heterocyclic Chemistry; Oxford, 1984; pp. 166-170.
[3]
Makaron, L.; Moran, C.A.; Namjoshi, O.; Rallapalli, S.; Cook, J.M.; Rowlett, J.K. Cognition-impairing effects of benzodiazepine-type drugs: Role of GABAA receptor subtypes in an executive function task in rhesus monkeys. Pharmacol. Biochem. Beh., 2013, 104, 62-68.
[4]
Allison, C.; Pratt, J.A. Neuroadaptive processes in GABAergic and glutamatergic systems in benzodiazepine dependence. Pharmacol. Therapeut., 2003, 98, 171-195.
[5]
Hawkins, E.J.; Malte, C.A. Prevalence and trends of benzodiazepine use among Veterans Affairs patients with posttraumatic stress disorder. Drug Alcohol Depend., 2012, 124, 154-161.
[6]
Banerji, A.; Goomer, N. A new synthesis of flavones. Synthesis, 1980, 11, 874-875.
[7]
Havsteen, B. Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol., 1983, 32, 1141-1148.
[8]
Cortés, E.; María, A.; Sanabria, H.; García, O. Synthesis and Spectral Properties of 11- [(o -; and p -substituted) is the clozapine that is an atypical antipsychotic agent with. J. Heterocyclic. Chem., 2002, 39, 55-57.
[9]
Wang, S-L.; Cheng, C.; Wu, F-Y.; Jiang, B.; Shi, F.; Tu, S-J.; Rajale, T.; Li, G. Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones. Tetrahedron, 2011, 67, 4485-4493.
[10]
Kaoua, R.; Nedjar-Kolli, B.; Roisnel, T.; Le Gal, Y.; Lorcy, D. Electroactive 1,5-benzodiazepines bearing either a tetrathiafulvalene or a ferrocene moiety. Tetrahedron, 2013, 69, 4636-4640.
[11]
Tonkikh, N.N.; Strakovs, A. 11-Aryl-3,3-dimethyl-7- and 7,8-Substituted 1, 2,3,4,10,11-Hexahydro-5H-dibenzo[b,e]-1,4-diazepin-1-ones. Chem. Hetero. Compd., 2004, 40, 7-8.
[12]
Tolpygin, I.E.; Mikhailenko, N.V. 11-R-dibenzo[b,e][1,4]diazepin-1-ones, the chemosensors for transition metal cations. Russ. J. Gen. Chem., 2012, 82, 1141-1147.
[13]
Sangshetti, J.N.; Chouthe, R.S. Green synthesis and anxiolytic activity of some new dibenz-[1,4] diazepine-1-one analogues. Arabian. J. Chem., 2013, 7, 415-419.
[14]
Cortes, C.A.; Valencia, A.L. New derivatives of dibenzo[b,e][1,4]dia-zepin‐1‐ones by an efficient synthesis and spectroscopy. J. Heterocycl. Chem., 2007, 44, 183-184.
[15]
Naeimi, H.; Moradian, M. Copper (I) -N2 S2 -salen type complex covalently anchored onto MCM-41 silica: An efficient and reusable catalyst for the A 3 -coupling reaction toward propargylamines. Appl. Organometal. Chem., 2013, 27, 300-306.
[16]
Naeimi, H.; Nejadshafiee, V. Efficient one-pot click synthesis of β-hydroxy-1,2,3-triazoles catalyzed by copper(i)@phosphorated SiO2via multicom-ponent reaction in aqueous media. New J. Chem., 2014, 38, 5429-5435.
[17]
Naeimi, H.; Nejadshafiee, V.; Masoum, S. Copper@PMO nanocomposites as a novel reusable heterogeneous catalyst for microwave-assisted green synthesis of β-hydroxy-1,2,3-triazoles through experimental design protocol. Appl. Organomet. Chem., 2015, 25, 314-321.
[18]
Naeimi, H.; Nejadshafiee, V.; Masoum, S. Highly efficient copper-imprinted functionalized mesoporous organosilica nanocomposites as a recyclable catalyst for click synthesis of 1,2,3-triazole derivatives under ultrasound irradiation: multivariate study by factorial design of experiments. RSC Adv, 2015, 5, 15006-15016.
[19]
Yang, X.; Chen, D.; Liao, S.; Song, H.; Li, Y.; Fu, Z.; Su, Y. High-performance Pd–Au bimetallic catalyst with mesoporous silica nanoparticles as support and its catalysis of cinnamaldehyde hydrogenation. J. Catal., 2012, 291, 36-43.
[20]
Yang, H.; Wang, Y.; Qin, Y.; Chong, Y.; Yang, Q.; Li, G.; Zhang, L.; Li, W. One-pot preparation of magnetic N-heterocyclic carbene-functionalized silica nanoparticles for the Suzuki–Miyaura coupling of aryl chlorides: improved activity and facile catalyst recovery. Green Chem., 2011, 13, 1352-1361.
[21]
Lee, Y-Y.; Wu, K.C-W. Conversion and kinetics study of fructose-to-5-hydroxymethylfurfural (HMF) using sulfonic and ionic liquid groups bi-functionalized mesoporous silica nanoparticles as recyclable solid catalysts in DMSO systems. Phys. Chem. Chem. Phys., 2012, 14, 13914-13917.
[22]
He, W.; Zhang, F.; Li, H. Active and reusable Pd(ii) organometallic catalyst covalently bonded to mesoporous silica nanospheres for water-medium organic reactions. Chem. Sci., 2011, 2, 961-966.
[23]
Gu, Y.; Ogawa, C.; Kobayashi, J.; Mori, Y.; Kobayashi, S. A heterogeneous silica‐supported scandium/ionic liquid catalyst system for organic reactions in water. Angew. Chem. Int. Ed., 2006, 118, 7375.
[24]
Magna, L.; Morvan, D. Ionic liquids and catalysis : Recent progress from knowledge to applications. Appl. Catal. A., 2010, 373, 1-56.
[25]
Ma, Z.; Yu, J.; Dai, S. Preparation of inorganic materials using ionic liquids. Adv. Mater., 2010, 22, 261-285.
[26]
Chen, Z.; Greaves, T.L.; Caruso, R.A.; Drummond, C.J. Long-range ordered lyotropic liquid crystals in intermediate-range ordered protic ionic liquid used as templates for hierarchically porous silica. J. Mater. Chem., 2012, 22, 10069-10076.
[27]
Sangsuwan, R.; Sangher, S.; Aree, T.; Mahidol, C. XRuchirawatab, S.; Kittakoop, P. An organocatalyst from renewable materials for the synthesis of coumarins and chromenes: three-component reaction and multigram scale synthesis. RSC Adv, 2014, 4, 13708-13718.
[28]
Miao, W.; Chan, T.H. Ionic-Liquid-Supported Organocatalyst: Efficient and Recyclable Ionic-Liquid-Anchored Proline for Asymmetric Aldol Reaction. Adv. Synth. Catal., 2006, 348, 1711-1718.
[29]
Tu, S-J.; Zhang, X-H.; Han, Z-G.; Cao, X-D.; Wu, S-S.; Yan, S.; Hao, W-J.; Ma, N. Synthesis of isoxazolo[5,4-b]pyridines by microwave-assisted multi-component reactions in water. J. Comb. Chem., 2009, 11, 428-432.
[30]
Jiang, B.; Li, C.; Shi, F.; Tu, S-J.; Kaur, P.; Wever, W.; Li, G. Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives. J. Org. Chem., 2010, 75, 2962-2965.
[31]
Ma, N.; Jiang, B.; Zhang, G.; Tu, S-J.; Wever, W.; Li, G. New multicomponent domino reactions (MDRs) in water: highly chemo-, regio- and stereoselective synthesis of spiro[1,3]dioxanopyridine-4,6-diones and pyrazolo[3,4-b]pyridines. Green Chem., 2010, 12, 1357-1361.
[32]
Jiang, B.; Tu, S-J.; Kaur, P.; Wever, W.; Li, G. Four-Component Domino Reaction Leading to Multifunctionalized. J. Am. Chem. Soc., 2009, 131, 11660-11661.
[33]
Naeimi, H.; Nejadshafiee, V.; Islami, M.R. Iron (III)-doped, ionic liquid matrix-immobilized, mesoporous silica nanoparticles: Application as recyclable catalyst for synthesis of pyrimidines in water. Micropor. Mesopor. Mate., 2016, 227, 23-30.
[34]
Leofanti, G.; Padovan, M.; Tozzola, G.; Venturelli, B. Surface area and pore texture of catalysts. Catal. Today, 1998, 41, 207-219.