An Update on Half-decade Recent Advances in Functionalized Fe3O4 Nanoparticles as Heterogeneous Nanocatalysts for the Synthesis of Six-Membered Compounds Containing Nitrogen: A Mini-Review

محورهای موضوعی : Iranian Journal of Catalysis

Faris Mohammed ¹ , Aseel M. Aljeboree ² , Nour Abd Alrazzak ³ , Ayad F. Alkaim ⁴ , Yasir Karim ⁵ , Sarah A. Hamood ⁶ , Ahmed B. Mahdi ⁷ , Mohammed Abed Jawad ⁸ , Salam Ahjel ⁹

1 - College of Science, University of Babylon, Iraq
2 - College of Science for women, University of Babylon, Iraq
3 - College of science for women, University of Babylon, Iraq
4 - College of Science for women, University of Babylon, Iraq
5 - Al-Manara College for Medical Sciences, Maysan, Iraq
6 - Al-Esraa University College, Baghdad, Iraq
7 - Anesthesia Techniques Department, Al-Mustaqbal University College, Babylon, Iraq
8 - Al-Nisour University College, Baghdad, Iraq
9 - Department of Pharmacy, Al-Zahrawi University College, Karbala, Iraq

تاریخ دریافت : 1401/02/02 تاریخ پذیرش : 1401/04/24 تاریخ انتشار : 1401/06/10

کلید واژه: magnetic, Synthesis, Nanocatalyst, Reusability, Fe3O4 nanoparticles, Heterocyclic compounds,

چکیده مقاله :

Over the past half-decade, the functionalized Fe3O4 nanoparticles have been applied to organic synthesis as heterogeneous nanocatalysts. Due to the magnetic properties, the functionalized Fe3O4 nanoparticles have been preferred over other catalytic systems. In addition, the unique physical, chemical, and magnetic field properties of Fe3O4 nanoparticles have led to the development of them for efficient organic synthesis as heterogeneous catalytic systems. Over the past half-decade, all the researchers tried to design and develop different functionalized Fe3O4 nanoparticles to perform the organic transformation. In this mini-review, different methodologies for the synthesis of six-membered compounds (heterocyclic compounds) containing nitrogen catalyzed by functionalized Fe3O4 nanoparticles have been reviewed. This short review aims to comprehensively investigate the use of functionalized Fe3O4 nanoparticles in the synthesis of six-membered compounds (heterocyclic compounds) containing nitrogen with emphasis on their reusability of the catalysts and magnetic field of them in separation from the organic reaction medium.

منابع و مأخذ:

[1] R.B. Sosman, J.C. Hostetter, THE OXIDES OF IRON. I. SOLID SOLUTION IN THE SYSTEM FE2O3—FE3O41, J. Am. Chem. Soc., 38 (1916) 807-833.

[2] E. Vitaku, D.T. Smith, J.T. Njardarson, Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals, J. Med. Chem., 57 (2014) 10257-10274.

[3] M.M. Heravi, V. Zadsirjan, Prescribed drugs containing nitrogen heterocycles: an overview, RSC Adv., 10 (2020) 44247-44311.

[4] S. Mohan, L. Sim, D.R. Rose, B.M. Pinto, Probing the active-site requirements of human intestinal N-terminal maltase-glucoamylase: Synthesis and enzyme inhibitory activities of a six-membered ring nitrogen analogue of kotalanol and its de-O-sulfonated derivative, Bioorg. Med. Chem., 18 (2010) 7794-7798.

[5] J.S. Carey, D. Laffan, C. Thomson, M.T. Williams, Analysis of the reactions used for the preparation of drug candidate molecules, Org. Biomol. Chem., 4 (2006) 2337-2347.

[6] M. Vatanparast, Z. Shariatinia, Revealing the role of different nitrogen functionalities in the drug delivery performance of graphene quantum dots: a combined density functional theory and molecular dynamics approach, Journal of Materials Chemistry B, 7 (2019) 6156-6171.

[7] Q. Deng, X. Meng, Recent Advances in the Cycloaddition Reactions of 2-Benzylidene-1-benzofuran-3-ones, and Their Sulfur, Nitrogen and Methylene Analogues, Chemistry – An Asian Journal, 15 (2020) 2838-2853.

[8] H. Dong, W. Li, J. Sun, S. Li, M.L. Klein, Understanding the Boron–Nitrogen Interaction and Its Possible Implications in Drug Design, J. Physic. Chem. B, 119 (2015) 14393-14401.

[9] Y.-J. Wu, N.A. Meanwell, Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design, J. Med. Chem., 64 (2021) 9786-9874.

[10] S. Dongbang, D.N. Confair, J.A. Ellman, Rhodium-Catalyzed C–H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles, Acc. Chem. Res., 54 (2021) 1766-1778.

[11] T.P. Andrejević, B. Warżajtis, B.Đ. Glišić, S. Vojnovic, M. Mojicevic, N.L. Stevanović, J. Nikodinovic-Runic, U. Rychlewska, M.I. Djuran, Zinc(II) complexes with aromatic nitrogen-containing heterocycles as antifungal agents: Synergistic activity with clinically used drug nystatin, J. Inorg. Biochem., 208 (2020) 111089.

[12] M. Savari, A. Varasteh-Moradi, S.Z. Sayyed-Alangi, Z. Hossaini, R. Zafarmehrabian, Ag/Fe3O4/TiO2@MWCNTs as a reusable organometallic nanocatalyst promoted green synthesis of new pyridobenzoazepines: Study of biological activity and reduction of organic pollutants, Appl. Organomet. Chem., 36 (2022) e6510.

[13] S. Motahari, A. Khazaei, Preparation and Characterization of Co (II) Supported on Modified Magnetic Fe3O4 Nanoparticles and Its Application as Catalyst for the Synthesis of 2-Amino-3-Cyanopyridines, Polycyclic Aromat. Compd., (2021) 1-12.

[14] E. Ezzatzadeh, F.Z. Hargalani, F. Shafaei, Bio-Fe3O4-MNPs Promoted Green Synthesis of Pyrido[2,1-a]isoquinolines and Pyrido[1,2-a]quinolines: Study of Antioxidant and Antimicrobial Activity, Polycyclic Aromat. Compd., (2021) 1-16.

[15] Z. Hossaini, N. Tabarsaei, S. Khandan, P. Valipour, M. Ghorchibeigi, ZnO/Ag/Fe3O4 nanoparticles supported on carbon nanotubes employing Petasites hybridus rhizome water extract: A novel organometallic nanocatalyst for the synthesis of new naphthyridines, Appl. Organomet. Chem., 35 (2021) e6114.

[16] A. Bamoniri, A. Mazoochi, S.A. Pourmousavi, Synthesis of 2,3-dihydroperimidines in the Presence of Nano-γ-Al2O3/BFn and Nano-γ-Al2O3/BFn/Fe3O4 as Catalysts under Different Conditions, Journal of Nanostructures, 11 (2021) 554-567.

[17] A. Moussa, A. Rahmati, Synthesis and characterization of silica-coated Fe3O4 nanoparticle@silylpropyl triethylammonium polyoxometalate as an organic–inorganic hybrid heterogeneous catalyst for the one-pot synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones, Appl. Organomet. Chem., 34 (2020) e5894.

[18] M. Mahmoodi Fard Chegeni, A. Bamoniri, A.A. Taherpour, One‐pot synthesis of 2H‐indazolo[2,1‐b]phthalazine‐triones via nano γ‐Al2O3/BF3/Fe3O4 as an efficient catalyst and theoretical DFT study on them, J. Heterocycl. Chem., 57 (2020) 2801-2814.

[19] M. Ghoorchibeigi, K. Larijani, P.A. Azar, K. Zare, I. Mehregan, ZnO/Fe3O4 nanoparticles promoted green synthesis of pyrazolo pyrimidinones: Study of antioxidant activity, J. Heterocycl. Chem., 57 (2020) 3612-3621.

[20] A. Zare, M. Barzegar, Dicationic ionic liquid grafted with silica-coated nano-Fe3O4 as a novel and efficient catalyst for the preparation of uracil-containing heterocycles, Res. Chem. Intermed., 46 (2020) 3727-3740.

[21] Z. Hossaini, A. Noushin, P. Valipour, M. Ghazvini, M.H. Rostam, Reusable Fe3O4/ZnO/MWCNTs Magnetic Nanocomposites Promoted Synthesis of New Naphthyridines, Polycyclic Aromat. Compd., (2020) 1-20.

[22] F. Shafaei, S. Sharafian, Green Synthesis of Imidazole Derivatives via Fe3O4-MNPs as Reusable Catalyst, J. Heterocycl. Chem., 56 (2019) 2644-2650.

[23] N. Faal Hamedani, M. Ghazvini, L. Azad, A. Noushin, Green synthesis of pyrido[2,1-a]isoquinolines and pyrido[1,2-a]quinolins using Fe3O4-MNPs as efficient nanocatalyst: Study of antioxidant activity, J. Heterocycl. Chem., 57 (2020) 337-345.

[24] M.A. Ashraf, Z. Liu, W.-X. Peng, C. Gao, New Copper Complex on Fe3O4 Nanoparticles as a Highly Efficient Reusable Nanocatalyst for Synthesis of Polyhydroquinolines in Water, Catal. Lett., 150 (2020) 683-701.

[25] M. Kalhor, Z. Zarnegar, Fe3O4/SO3H@zeolite-Y as a novel multi-functional and magnetic nanocatalyst for clean and soft synthesis of imidazole and perimidine derivatives, RSC Adv., 9 (2019) 19333-19346.

[26] S. Andalibi Salem, A. Khazaei, J.Y. Seyf, N. Sarmasti, M. Mahmoudiani Gilan, Preparation of Magnetic Cu(II) Nano-structure (Based on Nano-Fe3O4) and Application to the Synthesis of Hexahydroquinoline Derivatives, Polycyclic Aromat. Compd., 41 (2021) 319-332.

[27] E. Babaei, B.B.F. Mirjalili, One Pot Aqueous Media Synthesis of 1,3-Oxazine Derivatives Catalyzed by Reusable Nano-Al2O3/BF3/Fe3O4 at Room Temperature, Polycyclic Aromat. Compd., 41 (2021) 518-525.

[28] A. Karimiyan, S. Rostamizadeh, An Efficient Route to Imidazo[1,2-a]Pyridines and Pyrido[1,2-a]Pyrimidines via One-Pot Four-Component Reaction Using Fe3O4-GO-SO3H, Polycyclic Aromat. Compd., 41 (2021) 1483-1494.

[29] N. Basavegowda, K. Mishra, Y.R. Lee, Fe3O4-decorated MWCNTs as an efficient and sustainable heterogeneous nanocatalyst for the synthesis of polyfunctionalised pyridines in water, Materials Technology, 34 (2019) 558-569.

[30] P. Farokhian, M. Mamaghani, N.O. Mahmoodi, K. Tabatabaeian, A.F. Shojaie, An expeditious one-pot synthesis of pyrido[2,3-d]pyrimidines using Fe3O4–ZnO–NH2–PW12O40 nanocatalyst, J. Chem. Res., 43 (2019) 135-139.

[31] B.B.F. Mirjalili, R. Soltani, Nano-kaolin/Ti4+/Fe3O4: a magnetic reusable nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazoles, RSC Adv., 9 (2019) 18720-18727.

[32] M.A. Amrollahi, F. Vahidnia, Decoration of β-CD-ZrO on Fe3O4 magnetic nanoparticles as a magnetically, recoverable and reusable catalyst for the synthesis of 2,3-dihydro-1H-perimidines, Res. Chem. Intermed., 44 (2018) 7569-7581.

[33] E. Babaei, B.B.F. Mirjalili, One-pot synthesis of five substituted tetrahydropyridines using nano-Al2O3/BF3/Fe3O4 as a highly efficient nano-catalyst, Res. Chem. Intermed., 44 (2018) 3493-3505.

[34] M. Gholami Dehbalaei, N. Foroughifar, H. Pasdar, A. Khajeh-Amiri, N-Propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives, New J. Chem., 42 (2018) 327-335.

[35] N. Hazeri, S. Salahi, M. Lashkari, M.T. Maghsoodlou, E. Esmaeili-Shahri, E. Mollashahi, Facile Diastereoselective Synthesis of Functionalized Tetrahydropyridines Using Fe3O4/SiO2/TiO2 Nanocomposites, Org. Prep. Proced. Int., 50 (2018) 375-383.

[36] A. Khazaei, N. Sarmasti, J. Yousefi Seyf, Anchoring high density sulfonic acid based ionic liquid on the magnetic nano-magnetite (Fe3O4), application to the synthesis of hexahydroquinoline derivatives, J. Mol. Liq., 262 (2018) 484-494.

[37] B.B.F. Mirjalili, F. Aref, Nano-cellulose/BF3/Fe3O4: a magnetic bio-based nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazoles under solvent-free conditions, Res. Chem. Intermed., 44 (2018) 4519-4531.

[38] S. Sobhani, F. Nasseri, F. Zarifi, Unique role of 2-hydroxyethylammonium acetate as an ionic liquid in the synthesis of Fe3O4 magnetic nanoparticles and preparation of pyridine derivatives in the presence of a new magnetically recyclable heterogeneous catalyst, J. Iran. Chem. Soc., 15 (2018) 2721-2732.

[39] M. Abdi, S. Rostamizadeh, N. Zekri, An Efficient and Green Synthesis of 1′Hspiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione Derivatives in the Presence of Nano Fe3O4–GO–SO3H, Polycyclic Aromat. Compd., 39 (2019) 413-424.

[40] M. Beyki, M. Fallah-Mehrjardi, Silica Sulfuric Acid-coated Fe3O4 Nanoparticles as a Highly Efficient and Reusable Solid Acid Catalyst for the Green Synthesis of 2,3- Dihydroquinazolin-4(1H)-ones under Solvent-free Conditions, Lett. Org. Chem., 15 (2018) 39-44.

[41] B. Dam, R.A. Patil, Y.-R. Ma, A.K. Pal, Preparation, characterization and catalytic application of nano-Fe3O4-DOPA-SnO2 having high TON and TOF for non-toxic and sustainable synthesis of dihydroquinazolinone derivatives, New J. Chem., 41 (2017) 6553-6563.

[42] M. Fattahi, A. Davoodnia, M. Pordel, Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles, Russ. J. Gen. Chem., 87 (2017) 863-867.

[43] B.B.F. Mirjalili, M. Dehghani Tafti, Synthesis of quinoxalines promoted by eco-friendly nano-kaoline/BF3/Fe3O4 nano-catalyst under grinding condition, Sci. Iranica, 24 (2017) 3014-3021.

[44] H. Naeimi, S. Lahouti, Sonochemical one pot synthesis of novel spiroacridines catalyzed by magnetically functionalized Fe3O4 nanoparticles with chitosan as a reusable effective catalyst, RSC Adv., 7 (2017) 2555-2562.

[45] Q. Zhang, X.-M. Ma, H.-X. Wei, X. Zhao, J. Luo, Covalently anchored tertiary amine functionalized ionic liquid on silica coated nano-Fe3O4 as a novel, efficient and magnetically recoverable catalyst for the unsymmetrical Hantzsch reaction and Knoevenagel condensation, RSC Adv., 7 (2017) 53861-53870.