Functionalized Nano-Zeolite-NaY with –SO3H and Ca: Fabrication and its Catalytic Performance in the Four-Component Synthesis of Benzimidazolopyrimido Pyrimidines

Document Type : Research Article

Authors

Department of Chemistry, Payame Noor University, Tehran, I.R. IRAN

Abstract

In this study, solid zeolosulfuric acid (SO3H@zeolite-Y) was first obtained by the reaction of zeolite-NaY with chlorosulfonic acid. Ca2+ ions were then stabilized on the surface of zeolosulfuric acid by metal exchange method (Ca/SO3H@zeolite-Y). The structure and morphology of this new bi-functionalized nanoporous was investigated and identified using
FT-IR, FESEM, EDX and BET instrumental analyses. In the following, its catalytic activity in the synthesis of benzimidazo[2,1-a]pyrimido[5,4-d]pyrimidines through the four-component reaction of 2-amino benzimidazole, cyanoacetamide and two moles of different aromatic aldehydes under green conditions was considered. One of the obvious advantages of this nanocatalyst is the presence of Lewis (Ca2+) and Brunsted acid (-SO3H) sites on a nanoporous solid substrate, which can be very useful and important in multi-component syntheses. Simplicity of the procedure, the ability to recycle the catalyst and easy separation of the product, high yield and mild conditions are other advantages of this method.

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References

[1] Bacakova L., Vandrovcova M., Kopova I., Jirka I., Applications of ZEolites in Biotechnology and Medicine–A Review, Biomaterials science., 6(5): 974-989 (2018).
[2] اهالی آباده ز.، ایران نژاد م.، بررسی مدل‌های سینتیکی و هم‌دمایی حذف کادمیوم از محلول‌های آبی با کامپوزیت زئولیتی ـ آهنی، نشریه شیمی و مهندسی شیمی ایران، (۲)35: 99-111 (1395).
[3] Mofarahi M., Gholipour F., Gas Adsorption Separation of CO2/CH4 System using Zeolite 5, Microporous and Mesoporous Materials, 200: 1-10 (2014).
[4] Mažeikiene A., Rimeika, M., Valentukevičiene M., Oškinis V., Paškauskaite N., Brannvall E., Removal of Petroleum Products from Water using Natural Sorbent Zeolite, Journal of Environmental Engineering and Landscape Management, 13(4): 187-191 (2005).
[5] Khosravi K., Zendehdel M., Naserifar S., Tavakoli F., Khalaji K., Asgari A., Heteropoly Acid/NaY Zeolite as a Reusable Solid Catalyst for Highly Efficient Synthesis of Gem-Dihydroperoxides and 1,2,4,5-Tetraoxanes, J. Chem. Res, 40: 744-749 ( 2016).
Kalhor M., Zarnegar Z., Fe3O4/SO3H@zeolite-Y as a Novel Multi-Functional and Magnetic Nanocatalyst for Clean and Soft Synthesis of Imidazole and Perimidine Derivatives, RSC Advances, 9(34): 19333-19346 (2019).
[6] کلهر م.، سمیعی س.، میرشکرایی س.ا.، تهیه و شناسایی نانومزوپور دی‌اکسید منگنز/زئولیت-Y و کاربرد آن به‌عنوان یک نانوکاتالیست مؤثر در سنتز اتیل بنزایمیدازولیل-۲- آمینو تیو استات­ها از روش یک واکنش سه‌جزئی در شرایط سبز،  نشریه شیمی و مهندسی شیمی ایران، (۱)41: ۱-۱3 (۱401).
[7] Estevez R., Iglesias I., Luna D., Bautista F.M., Sulfonic Acid Functionalization of Different Zeolites and their use as Catalysts in the Microwave-Assisted Etherification of Glycerol with Tert-Butyl Alcohol. Molecules, 22(12): 2206 (2017).
[8] Kumar D., Khan S.I., Tekwani B.L., Ponnan P., Rawat D.S., 4-Aminoquinoline-Pyrimidine Hybrids: Synthesis, Antimalarial Activity, Heme Binding and Docking Studies, European Journal of Medicinal Chemistry, 89: 490-502 (2015).
[9] Cocco M.T., Congiu C., Onnis V., Piras R., Synthesis and Antitumor Evaluation of 6-Thioxo-, 6-Oxo-and 2, 4-Dioxopyrimidine Derivatives, IL Farmaco., 56(10): 741-748 (2001).
[10] Ashour H.M., Shaaban O.G., Rizk O.H., El-Ashmawy I.M., Synthesis and Biological Evaluation of Thieno [2′, 3′: 4, 5] Pyrimido [1, 2-b][1, 2, 4] Triazines and Thieno [2, 3-d][1, 2, 4] Triazolo [1, 5-a] Pyrimidines as Anti-Inflammatory and Analgesic Agents, European Journal of Medicinal Chemistry., 62: 341-351(2013).
[11] Nielsen-Kudsk F., Pedersen A.K., Pharmacokinetics of Dipyridamole, Acta Pharmacologica et Toxicologica, 44(5): 391–9 (1979).
[12] Masur H., Brooks J.T., Benson C.A., Holmes K.K., Pau A.K., Kaplan J.E., Prevention and Treatment of Opportunistic Infections in HIV-Infected Adults and Adolescents, Clinical Infectious Diseases, 58(9): 1308–1311 (2014).
[13] Moore A.Y., Clinical Applications for Topical 5-Fluorouracil in the Treatment of Dermatological Disorders, The Journal of Dermatological Treatment, 20(6): 328–335 (2009).
[14] Nawrocka W., Sztuba B., Kowalska M.W., Liszkiewicz H., Wietrzyk J., Nasulewicz A., Pełczyńska M., Opolski A., Synthesis and Antiproliferative Activity in Vitro of 2-Aminobenzimidazole Derivative, IL Farmaco, 59: 83–91 (2004).
[15] Shahi M., Foroughifar N., Mobinikhaledi A., Synthesis and Antimicrobial Activity of some Tetrahydro Quinolone Diones and Pyrano[2,3-d]Pyrimidine Derivatives, Iranian Journal of Pharmaceutical Research, 14: 757-763 (2015).
[16] Mobinikhaldeia A., Foroughifarb N., Moghanianc H., Jaberia H.R., One-pot Synthesis of Some Novel 2-[(Z)-1-(Aryl)]-6,7-dihydro-2H-istohiazolo[2,3-a]pyrimidine-3(5H)-one Derivatives, Organic Chemistry Research, 4(1): 95-99 (2018).
[17] Abaszadeh, M., Seifi M., KF/Al2O3: As a Solid Phase and Recyclable Basic Catalyst for Synthesis Mono and Bis Pyrimidine Derivatives. Iran. J. Chem. Chem. Eng, 36(1): 35-43(2017)
[18] Gastpar H., The Inhibition of the Cancer Stickiness by Pyrimido-Pyrimidine Derivates Induced by Inhibition of Platelet Aggregation, Acta Medica Scandinavica Supplementum, 525: 269-271 (1972).
[19] Bunag R. D., Douglas C. R., Imai S., Berne R. M., Influence of a pyrimidopyrimidine derivative on deamination of adenosine by blood, Circulation Research, 15(1): 83-88 (1964).
[20] Emmons P.R., Harrison M.J.G., Honour A.J., Mitchell J.R.A., Effect of a Pyrimidopyrimidine Derivative on Thrombus Formation in the Rabbit, Nature, 208: 255-257 (1965).
[21] De la Cruz J.P., Carrasco T., Ortega G., De la Cuesta F.S., Inhibition of Ferrous-Induced Lipid Peroxidation by Pyrimido-Pyrimidine Derivatives in Human Liver Membranes, Lipids, 27(3): 192-194 (1992).
[22] Fang Y., Xu, J., Li Z., Yang Z., Xiong  L., Jin Y., Chang S., Design and Synthesis of Novel Pyrimido [5, 4-d] Pyrimidine Derivatives as GPR119 Agonist for Treatment of Type 2 Diabetes, Bioorganic Medicinal Chemistry, 26(14): 4080-4087 (2018).
[23] Haggarty S.J., Mayer T.U., Miyamoto D.T., Fathi R., King R.W., Mitchison T.J., Schreiber S.L., Dissecting Cellular Processes using Small Molecules: Identification of Colchicine-Like, Taxol-Like and other Small Molecules that Perturb Mitosis, Chemistry Biology, 7(4): 275-286 (2000).
[24] Reddy M.V., Kim J.S., Lim K.T., Jeong Y.T., Polyethylene Glycol (PEG-400): an Efficient Green Reaction Medium for the Synthesis of Benzo [4,5] Imidazo[1,2-a]-Pyrimido [4,5-d] Pyrimidin-4 (1H)-Ones under Catalyst-Free Conditions, Tetrahedron Letters, 55(47): 6459-6462 (2014).
[25] Liu J., Lei M., Hu L., A Catalyst-Free Reaction in Water: Synthesis of Benzo [4,5] Imidazo[1,2-a] Pyrimido [4,5-d] Pyrimidin-4 (1H)-One Derivatives, Green Chemistry, 14(9): 2534-2539 (2012).
[26] Abdelazeem N., Basyouni W., Abbas S., El-Bayouki K., El-kady M., Silica Sulfuric Acid/Ethylene Glycol: An Efficient Eco-Friendly Catalyst for One-Pot Synthesis of Tricyclic and Tetarcyclic Dihydropyrimidine Derivatives, Egyptian Journal of Chemistry, 62(12): 2265-2276 (2019).
[27] Kalhor M., Zarnegar Z., Fe3O4/SO3H@zeolite-Y as a Novel Multi-Functional and Magnetic Nanocatalyst for Clean and Soft Synthesis of Imidazole and Perimidine Derivatives, RSC Advances, 9(34): 19333-19346 (2019).
[28] Kalhor M., Banibairami S., Mirshokraie S.A., Ni@zeolite-Y Nanoporous; a Valuable and Efficient Nanocatalyst for the Synthesis of N-Benzimidazole-1, 3-Thiazolidinones, Green Chemistry Letters and Reviews, 11(3): 334-344 (2018).
[29] Kalhor M., Zarnegar Z., Fe3O4/SO3H@zeolite-Y as a Novel Multi-Functional and Magnetic Nanocatalyst for Clean and Soft Synthesis of Imidazole and Perimidine Derivatives, RSC Advances, 9: 19333-19346 (2019).
[30] Kalhor M., Zarnegar Z., Seyedzade Z., Banibairami S., SO3H-Functionalized Zeolite-Y as an Efficient Nanocatalyst for the Synthesis of N-Benzimidazole-2-Aryl-4-Thiazolidinones and Tri-Substituted Imidazoles, Current Organic Synthesis, 17(2): 117-130 (2020).
[31] Perez-Pariente J., Martens J.A., Jacobs P.A., Crystallization Mechanism of Zeolite Beta from (TEA)2O, Na2O and K2O Containing Aluminosilicate Gels, Applied Catalysis, 31(1): 35-64 (1987).
[32] Yang C., Xu Q., Aluminated Zeolites β and their Properties, Part 1. Alumination of Zeolites β, Journal of the Chemical Society, Faraday Transactions, 93(8): 1675-1680 (1997).
[33] Endang P.S., Rahadian A.R., Ulva T.I.M., Alvin R.W., Rendy M.I., Nurul W., The MnO2/Zeolite NaY Catalyzed Oxidation of CO Emission in Catalytic Converter System, In Materials Science Forum, 964: 199-208 (2019).

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