طراحی و ساخت کمپلکس حلقوی تیوکربوهیدرازید/مس بر پایه نانوذره های مغناطیسی و به کارگیری آن به عنوان یک نانوکاتالیزگر کارآمد و قابل بازیافت نوین برای سنتز چندجزئی 2-آمینو - H۴- کرومن ها در محیط آبی

نوع مقاله : علمی-پژوهشی

نویسندگان

1 دانشکده شیمی، دانشگاه دامغان، دامغان، ایران

2 گروه شیمی، دانشکده علوم پایه، دانشگاه پیام نور، تهران، ایران

چکیده

در این پژوهش،  براساس یافته ­های قبلی، ابتدا نانوذره­ های مغناطیسی با روش هسته ـ پوسته با ذره­ های سیلیکون دی­ اکسید پوشانده شده و با واکنش با 3-کلروپروپیل تری­اتوکسی سیلان و سپس با لیگاند آلی تیوکربوهیدرازید (SiO2-TCH@Fe3O4) عامل‌دار شد. سپس یون‌های مس بر روی نانوبستر سیلیکاتی تثبیت شد (SiO2-TCH/Cu@Fe3O4). ساختار نانوذره­ های تهیه شده به عنوان یک هیبرید آلی ـ فلزی مغناطیسی با استفاده از روش‌های FT-IR، FESEM، XRD، EDX، TGA، VSM و BET مورد بررسی و تأیید  قرار گرفت. در ادامه، فعالیت کاتالیزگری آن در سنتز تعدادی از مشتق ­های 4-آریل-2-آمینوکرومن­ ها از طریق واکنش تراکمی سه جزئی آلدئیدهای آروماتیک، مالونیتریل و دیمدون، مورد بررسی قرار گرفت. مزایای این روش ازجمله ارزان­، ایمن و  قابلیت استفاده مجدد نانوکاتالیست، جداسازی آسان کاتالیست ناهمگن از محیط واکنش، زمان کوتاه انجام واکنش، بازده بالا، جداسازی آسان و سریع فراورده و استفاده از حلال غیرسمی آب، موجب شده که این روش در عین سادگی، در حوزه «شیمی سبز» قرار بگیرد.

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مراجع

[1] Lu J., Toy P. H. Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization. Chemical Reviews, 109(2): 815-838 (2009).
[2] Zhang Z. H., Lu H. Y., Yang S. H., Gao J. W. Synthesis of 2, 3-Dihydroquinazolin-4 (1 H)-Ones by Three-Component Coupling of Isatoic Anhydride, Amines, and Aldehydes Catalyzed by Magnetic Fe3O4 Nanoparticles in Water. Journal of Combinatorial Chemistry, 12(5): 643-646 (2010).
[3] Zhu Y., Fang Y., Kaskel S. Folate-Conjugated Fe3O4@SiO2 Hollow Mesoporous Spheres for Targeted Anticancer Drug Delivery. The Journal of Physical Chemistry C, 114: 16382-16388 (2010).
[4] Neuberger T., Schöpf B., Hofmann H., Hofmann M., Von Rechenberg B. Superparamagnetic Nanoparticles for Biomedical Applications: Possibilities and Limitations of a New Drug Delivery System. Journal of Magnetism and Magnetic Materials, 293(1): 483-496 (2005).
[5] Pankhurst Q. A., Connolly J., Jones S. K., Dobson J. Applications of Magnetic Nanoparticles in Biomedicine. Journal of Physics D: Applied Physics, 36(13): R167 (2003).
[6] Graham D. L., Ferreira H. A., Freitas P. P. Magnetoresistive-Based Biosensors and Biochips. TRENDS in Biotechnology, 22(9): 455-462 (2004).
[7]  Wang D., He J., Rosenzweig N., Rosenzweig Z. Superparamagnetic Fe2O3 Beads− CdSe/ZnS Quantum Dots Core− Shell Nanocomposite Particles for Cell Separation. Nano Letters, 4(3): 409-413(2004).
[8] Jordan A., Scholz R., Wust P., Fähling H., Felix R. Magnetic Fluid Hyperthermia (MFH): Cancer Treatment with AC Magnetic Field Induced Excitation of Biocompatible Superparamagnetic Nanoparticles. Journal of Magnetism and Magnetic Materials, 201(1-3): 413-419 (1999).
[9] Hu A., Yee G. T., Lin W. Magnetically Recoverable Chiral Catalysts Immobilized on Magnetite Nanoparticles for Asymmetric Hydrogenation of Aromatic Ketones. Journal of the American Chemical Society, 127(36): 12486-12487 (2005).
[10] Senapati K. K., Borgohain C., Phukan P. Synthesis of Highly Stable CoFe2O4 Nanoparticles and Their Use as Magnetically Separable Catalyst for Knoevenagel Reaction in Aqueous Medium. Journal of Molecular Catalysis A: Chemical, 339(1-2): 24-31 (2011).
[11] Lim C. W., Lee I. S. Magnetically Recyclable Nanocatalyst Systems for the Organic Reactions. Nano Today, 5(5): 412-434 (2010).
[12] Safari J., Banitaba S. H., Khalili S. D. Cellulose Sulfuric Acid Catalyzed Multicomponent Reaction for Efficient Synthesis of 1, 4-Dihydropyridines Via Unsymmetrical Hantzsch Reaction in Aqueous Media. Journal of Molecular Catalysis A: Chemical, 335(1-2): 46-50 (2011).
[13] Shen M., Driver T. G. Iron (II) Bromide-Catalyzed Synthesis of Benzimidazoles from Aryl Azides. Organic letters, 10(15): 3367-3370‏ (2008).
[14] Bahrami K., Khodaei M.M., Naali F. Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles. The Journal of organic chemistry, 73(17): 6835-6837 (2008).
[15] Singh M. S., Chowdhury S. Recent Developments in Solvent-Free Multicomponent Reactions: A Perfect Synergy for Eco-Compatible Organic Synthesis. RSC Advances, 2: 4547–4592 (2012).
[16] Ellis G. P. “The Chemistry of Heterocyclic Compounds in Chromenes, Chromanes, and Chromones”, Edited. by A. Weissberger, EC Taylor (1977).
[17] Galil F. A., Riad B. Y., Sherif S. M., Elnagdi M. H. Activated Nitriles in Heterocyclic Synthesis: A Novel Synthesis of 4-Azoloyl-2-Amino Quinzolines. Chemistry Letters, 1123-1126 (1982).
[18] Varma R. S., Dahiya R. An Expeditious and Solvent-Free Synthesis of 2-Amino-Substituted Isoflav-3-Enes Using Microwave Irradiation. The Journal of Organic Chemistry, 63(22): 8038-8041 (1998).
[19] RW D., Currie K S., Mitchell S. A., Darrow J. W., Pippin D. A. Comb. Chem. High Throughput Screening, 7: 473 (2004).
[20] Patchett A. A., Nargund R. P., Privileged Structures—An Update (2000).
[21] Bonsignore L., Loy G., Secci D., Calignano A., Synthesis and Pharmacological Activity of 2-Oxo-(2H) 1-Benzopyran-3-Carboxamide Derivatives. European Journal of Medicinal Chemistry, 28(6): 517-520 (1993).
[22] Zhang, G., Zhang, Y., Yan, J., Chen, R., Wang, S., Ma, Y., & Wang, R. One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and 2-Amino-4 H-Chromenes: Discovery of a Type of Potent Antibacterial Agent. The Journal of organic chemistry, 77(2): 878-888 (2012).
[23] Kakanejadifard A., Azarbani F., Khosravani N., Notash B. Synthesis, Structural Characterization, X-Ray, Solvatochromism and Biological Properties of 7-Hydroxy-2-(2-Hydroxy-5-(Phenyldiazenyl) Benzylidene) Amino)-4-Phenyl-4H-Chromene-3-Carbonitrile. Journal of Molecular Liquids, 221: 211-215. (2016).
[24] Sabry N. M., Mohamed H. M., Khattab E. S. A., Motlaq S. S., El-Agrody A. M. Synthesis of 4H-Chromene, Coumarin, 12H-Chromeno [2, 3-d] Pyrimidine Derivatives and Some of Their Antimicrobial and Cytotoxicity Activities. European journal of medicinal chemistry, 46(2): 765-772 (2011).
[25] Skommer J., Wlodkowic D., Mättö M., Eray, M., Pelkonen J. HA14-1, A Small Molecule Bcl-2 Antagonist, Induces Apoptosis and Modulates Action of Selected Anticancer Drugs in Follicular Lymphoma B Cells. Leukemia research, 30(3): 322-331 (2006).
[26] Kemnitzer W., Kasibhatla S., Jiang S., Zhang H., Zhao J., Jia S., Vaillancourt L. Discovery of 4-Aryl-4H-Chromenes as a New Series of Apoptosis Inducers Using a Cell-and Caspase-Based High-Throughput Screening Assay. 2. Structure–Activity Relationships of the 7-and 5-, 6-, 8-Positions. Bioorganic & medicinal chemistry letters, 15(21): 4745-4751 (2005).
[27] Gourdeau H., Leblond L., Hamelin B., Desputeau C., Dong K., Kianicka I., Custeau D., Bourdeau C., Geerts L., Cai S. X., Drewe J., Labrecque D., Kasibhatla S., Tseng B., Antivascular and Antitumor Evaluation of 2-Amino-4-(3-Bromo-4,5-Dimethoxy-Phenyl)-3-Cyano-4H-Chromenes, a Novel Series of Anticancer Agents. Molecular Cancer  Therapeutics, 3: 1375-1383 (2004).
[28] Brahmachari G., Banerjee B., Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano-4 H-Pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst. ACS Sustainable Chemistry & Engineering, 2(3): 411-422 (2014).
[29] Yang F., Wang H., Jiang L., Yue H., Zhang H., Wang Z., Wang L., A Green and One-Pot Synthesis of Benzo[g]Chromene Derivatives Through a Multi-Component Reaction Catalyzed by Lipase. RSC Advances, 5: 5213-5216 (2015).
[30] Shaabani A., Ghadari R., Ghasemi S., Pedarpour M., Rezayan A. H., Sarvary A., Ng, S. W. Novel One-Pot Three-and Pseudo-Five-Component Reactions: Synthesis of Functionalized Benzo [g]-and Dihydropyrano [2, 3-g] Chromene Derivatives. Journal of Combinatorial Chemistry, 11(6): 956-95‏ (2009).
[31] Mobinikhaledi A., Moghanian H., Ghanbari M. Synthesis and Characterization of Sodium Polyaspartate‐Functionalized Silica‐Coated Magnetite Nanoparticles: A Heterogeneous, Reusable and Magnetically Separable Catalyst for the Solvent‐Free Synthesis of 2‐Amino‐4H‐Chromene Derivatives. Applied Organometallic Chemistry, 32(3): e4108‏ (2018).
[32] Davarpanah J., Kiasat A. R., Noorizadeh S., Ghahremani M. Nano Magnetic Double-Charged Diazoniabicyclo [2.2. 2] Octane Dichloride Silica Hybrid: Synthesis, Characterization, and Application as an Efficient and Reusable Organic–Inorganic Hybrid Silica with Ionic Liquid Framework for One-Pot Synthesis of Pyran Annulated Heterocyclic Compounds in Water. Journal of Molecular Catalysis A: Chemical, 376: 78-89 (2013).
[33] Yang G., Luo C., Mu X., Wang T., Liu X. Y. Highly Efficient Enantioselective Three-Component Synthesis of 2-Amino-4 H-Chromenes Catalysed by Chiral Tertiary Amine-Thioureas. Chemical Communications, 48(47): 5880-5882 (2012).
[34] Kabalka G. W., Venkataiah B., Das B. C., Synthesis of 2H-Chromenes in Ionic Liquid Solvents. Synlett, 12: 2194-2196 (2004).
[35] Makarem S., Mohammadi A. A., Fakhari A. R. A Multi-Component Electro-Organic Synthesis of 2-Amino-4H-Chromenes. Tetrahedron Letters, 49(50): 7194-7196‏ (2008).
[36] Shaabani A., Ghadari R., Ghasemi S., Pedarpour M., Rezayan A. H., Sarvary A., Ng S. W. Novel One-Pot Three-and Pseudo-Five-Component Reactions: Synthesis of Functionalized Benzo [g]-and Dihydropyrano [2, 3-g] Chromene Derivatives. Journal of Combinatorial Chemistry, 11(6): 956-959 (2009).
[37] Khurana J. M., Nand B., & Saluja P. DBU: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted 3, 4-Dihydropyrano [3, 2-c] Chromenes, Dihydropyrano [4, 3-b] Pyranes, 2-Amino-4H-Benzo [h] Chromenes and 2-Amino-4H Benzo [g] Chromenes in Aqueous Medium. Tetrahedron, 66(30): 5637-5641 (2010).
[38] Kalhor M., Rezaee‐Baroonaghi F., Dadras A., Zarnegar Z. Synthesis of New TCH/Ni‐Based Nanocomposite Supported on SBA‐15 and Its Catalytic Application for Preparation of Benzimidazole and Perimidine Derivatives. Applied Organometallic Chemistry, 33(5): e4784. (2019).
[39] مهدی کلهر.، سیما سمیعی.، سید احمد میرشکرایی.، تهیه و شناسایی نانومزوپور دی اکسید منگنز/زئولیت-Y و کاربرد آن به‌عنوان یک نانو کاتالیزگر مؤثر در سنتز اتیل بنزایمیدازولیل-۲- آمینو تیو استات­ها از طریق یک واکنش سه‌جزئی در شرایط سبز.  نشریه شیمی و مهندسی شیمی ایران، (۱)41:  ۱تا۱3 (۱401).
[40] Andalibi Salem S., Khazaei A., Seyf J. Y., Sarmasti N., Mahmoudiani Gilan, M. Preparation of Magnetic Cu (II) Nano-Structure (Based on Nano-Fe3O4) and Application to the Synthesis of Hexahydroquinoline Derivatives. Polycyclic Aromatic Compounds, 1-14‏ (2019).
[41] Kalhor, M., Sajjadi, S. M., Dadras, A. Cu/TCH-pr@ SBA-15 Nano-Composite: A New Organometallic Catalyst for Facile Three-Component Synthesis of 4-Arylidene-Isoxazolidinones. RSC Advances, 10(46): 27439-27446‏ (2020).
[42] Alizadeh, A., Khodaei, M. M., Kordestania, D., Beygzadeh, M. A Biguanide/Pd-Decorated SBA-15 Hybrid Nanocomposite: Synthesis, Characterization and Catalytic Application. Journal of Molecular Catalysis A: Chemical, 372: 167-174‏ (2013).
[43] Hu, J., Zou, Y., Liu, J., Sun, J., Yang, X., Kan, Q., Guan, J. Immobilization of Cu-Chelate Onto SBA-15 for Partial Oxidation of Benzyl Alcohol Using Water as the Solvent. Research on Chemical Intermediates, 41(8): 5703-5712 (2015).
[44] Sarkar, K., Dhara, K., Nandi, M., Roy, P., Bhaumik, A., Banerjee, P. Selective Zinc (II)‐Ion Fluorescence Sensing by a Functionalized Mesoporous Material Covalently Grafted with a Fluorescent Chromophore and Consequent Biological Applications. Advanced Functional Materials, 19(2): 223-234‏ (2009).
[45] Siddiqui, S. A., Narkhede, U. C., Palimkar, S. S., Daniel, T., Lahoti, R. J., Srinivasan, K. V. Room Temperature Ionic Liquid Promoted Improved and Rapid Synthesis of 2, 4, 5-Triaryl Imidazoles from Aryl Aldehydes and 1, 2-Diketones or α-Hydroxyketone. Tetrahedron, 61(14): 3539-3546 (2005).
[46] Xu, H., Tong, N., Cui, L., Lu, Y., Gu, H. Preparation of Hydrophilic Magnetic Nanospheres with High Saturation Magnetization. Journal of magnetism and magnetic materials, 311(1): 125-130 (2007).
[47] Mobinikhaledi, A., Fard, M. A. B. Tetrabutylammonium Bromide in Water as a Green Media for the Synthesis of Pyrano [2, 3-d] Pyrimidinone and Tetrahydrobenzo [b] Pyran Derivatives. Acta Chim. Slov, 57(4): 931-935‏ (2010).
[48] Qareaghaj, O. H., Mashkouri, S., Naimi-Jamal, M. R., Kaupp, G. Ball Milling for the Quantitative and Specific Solvent-Free Knoevenagel Condensation+ Michael Addition Cascade in the Synthesis of Various 2-Amino-4-Aryl-3-Cyano-4 H-Chromenes Without Heating. RSC Advances, 4(89): 48191-48201 (2014).
[49] Boumoud, B., Yahiaoui, A. A., Boumoud, T., Debache, A. Available Online www. jocpr. com. Journal of Chemical and Pharmaceutical Research, 4(1): 795-799 (2012).
[50] Niknam, K., Borazjani, N., Rashidian, R., Jamali, A. Silica-Bonded N-Propylpiperazine Sodium N-Propionate as Recyclable Catalyst for Synthesis of 4H-Pyran Derivatives. Chinese Journal of Catalysis, 34(12): 2245-2254‏ (2013).
[51] Baghbanian, S. M., Rezaei, N., Tashakkorian, H. Nanozeolite Clinoptilolite as a Highly Efficient Heterogeneous Catalyst for the Synthesis of Various 2-Amino-4 H-Chromene Derivatives in Aqueous Media. Green Chemistry, 15(12): 3446-3458. (2013).
[52] Maleki B., Ashrafi S. S. Nano α-Al2O3 Supported Ammonium Dihydrogen Phosphate (NH4 H2PO4/Al2O3): Preparation, Characterization and Its Application as a Novel and Heterogeneous Catalyst for the One-Pot Synthesis of tetrahydrobenzo [b] pyran and pyrano [2,3-c] pyrazole derivatives. RSC Advances, 4(81): 42873-42891 (2014).

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