Abstract
5-Substituted-1H-tetrazoles were synthesized via the [3 + 2] cycloaddition of NaN3 and several nitriles using Cu1-xCoxFe2O4 (x = 0, 0.25, 0.5, 0.75, and 1) nanocatalysts in N,N-dimethylformamide (DMF) at 120 °C. The Cu0.5Co0.5Fe2O4 nanospinel ferrite is the most active nanocatalyst in comparison to other prepared nanocatalysts. This nanocatalyst was easily separated from the reaction mixture using an external magnet and reused for five cycles without any appreciable loss of catalytic activity. The cost-effective and easy availability of the catalyst, simple methodology, high yield, and easy workup are the extra advantages of this method. The structural characteristics of the catalyst were investigated by scanning electron microscopy, X-ray diffraction, and vibrating sample magnetometer analyses.
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References
Abrishami F, Daryanavard M, Nakhaei F (2023) Synthesis of 5-substituted-1H-tetrazoles using zinc zirconium phosphate and copper zirconium phosphate as reusable heterogeneous catalysts. J Iran Chem Soc 20:1821–1829
Aghavandi H, Ghorbani-Choghamarani A (2022) ZnFe2O4@ L-Arginine-Ni: a novel, green, recyclable, and highly versatile catalyst for the synthesis of 1H-tetrazoles and oxidation of sulfides to the sulfoxides. J Phys Chem Solids 170:110952
Agrawal JP (2005) Some new high energy materials and their formulations for specialized applications. Prop Explos Pyrotech 30:316–328
Bonnamour J, Bolm C (2009) Iron salts in the catalyzed synthesis of 5‐substituted 1H‐tetrazoles. Chem Eur J 15:4543–4545
Du Z, Si C, Li Y, Wang Y, Lu J (2012) Improved synthesis of 5-substituted 1 H-tetrazoles via the [3+2] cycloaddition of nitriles and sodium azide catalyzed by silica sulfuric acid. Int J Mol Sci 13:4696–4703
Duncia JV, Pierce ME, Santella JB (1991) Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole. J Org Chem 56:2395–2400
Fareghi-Alamdari R, Zandi F, Keshavarz MH (1921) Copper–cobalt synergy in Cu1−xCoxFe2O4 spinel ferrite as a highly efficient and regioselective nanocatalyst for the synthesis of 2, 4-dinitrotoluene. RSC Adv 5(88):71911–71917
Fareghi-Alamdari R, Hosseinabadi Z, Farhadi Khouzani M (2012) Synthesis, characterization and investigation of catalytic activity of Cu1−xCoxFe2O4 nanocatalysts in t-butylation of p-cresol. J Chem Sci 124:827–834
Fareghi-Alamdari R, Golestanzadeh M, Zekri N (2014) Application of nanosized Cu0.5Co0.5Fe2O4 spinel ferrite as a nanocatalyst in the synthesis of 14‐aryl‐14H‐dibenzo [a, j] xanthene derivatives under solvent‐free conditions. J Chin Chem Soc 61:1341–1350
Fatahi H, Jafarzadeh M, Pourmanouchehri Z (2019) Synthesis of α‐aminonitriles and 5‐substituted 1 H‐tetrazoles using an efficient nanocatalyst of Fe3O4@ SiO2–APTES‐supported trifluoroacetic acid. J Heterocycl Chem 56:2090–2098
Gautam S, Muthurani S, Balaji M, Thakur P, Pathinettam Padiyan D, Chae KH, Kim SS, Asokan K (2011) Electronic structure studies of nanoferrite CuxCo1–xFe2O4 by X-ray absorption spectroscopy. J Nanosci Nanotechnol 11:386–390
Ghadermazi M, Molaei S, Ghadermazi N (2021) Introduction of Fe into mesoporous MCM-41 for the synthesis of 5-substituted 1H-tetrazoles from aryl nitriles in water. Microporous Mesoporous Mater 328:111441
Ghadermazi M, Molaei S, Khorami S (2023) Synthesis, characterization and catalytic activity of copper deposited on MCM-41 in the synthesis of 5-substituted 1 H-tetrazoles. J Porous Mater 30:949–963
Hantzsch A, Vagt A (1901) Ueber das sogenannte diazoguanidin. Eur J Org Chem 314:339–369
Jaroslav R, Vávrová K, Hrabálek A (2012) Synthesis and functionalization of 5‐substituted tetrazoles. Eur J Org Chem 2012:6101–6118
Jin T, Kitahara F, Kamjio S, Yamamoto Y (2008) Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide. Tetrahedron Lett 49:2824–2827
Kal-Koshvandi AT, Maleki A, Tarlani A, Soroush MR (2020) Synthesis and characterization of ultrapure HKUST-1 MOFs as reusable heterogeneous catalysts for the green synthesis of tetrazole derivatives. ChemistrySelect 5:3164–3172
Kant R, Singh V, Agarwal A (2016) An efficient and economical synthesis of 5-substituted 1H-tetrazoles via Pb(II) salt catalyzed [3+2] cycloaddition of nitriles and sodium azide. C R Chim 19:306–313
Kantam ML, Shiva Kumar KB, Sridhar C (2005) Nanocrystalline ZnO as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles. Adv Synth Catal 347:1212–1214
Khalili D, Rezaee M (2019) Impregnated copper ferrite on mesoporous graphitic carbon nitride: an efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1, 2, 3‐triazoles and tetrazoles. Appl Organomet Chem 33:e5219
Khalili D, Evazi R, Neshat A, Aboonajmi J (2021) Copper (I) complex of dihydro bis (2‐mercapto benzimidazolyl) borate as an efficient homogeneous catalyst for the synthesis of 2H‐indazoles and 5‐substituted 1H‐tetrazoles. ChemistrySelect 6:746–753
Klapötke TM, Sabate CM (2008) Bistetrazoles: nitrogen-rich, high-performing, insensitive energetic compounds. Chem Mater 20:3629–3637
Koolivand M, Nikoorazm M, Ghorbani-Choghamarani A, Mohammadi M (2022) A novel cubic Zn‐citric acid‐based MOF as a highly efficient and reusable catalyst for the synthesis of pyranopyrazoles and 5‐substituted 1H‐tetrazoles. Appl Organomet Chem 36:e6656
Kulkarni PA, Satpati AK, Thandavarayan M, Shendage SS (2021) An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles. Chem Pap 75:2891–2899
Kumar S, Kumar A, Agarwal A, Awasthi SK (2015) Synthetic application of gold nanoparticles and auric chloride for the synthesis of 5-substituted 1H-tetrazoles. RSC Adv 5:21651–21658
Lakshmi Kantam M, Shiva Kumar KB, Phani Raja K (2006) An efficient synthesis of 5-substituted 1H-tetrazoles using Zn/Al hydrotalcite catalyst. J Mol Catal A Chem 247:186–188
Mancheño OG, Bolm C (2007) Synthesis of N-(1 H)-tetrazole sulfoximines. Org Lett 9:2951–2954
Mazloumi M, Shirini F (2023) Acidic ionic liquid bridge supported on nano rice husk ash: an efficient promoter for the conversion of nitriles to their corresponding 5‐substituted 1H‐tetrazoles and amides. ChemistrySelect 8:e202203554
Moeini N, Tamoradi T, Ghadermazi M, Ghorbani-Choghamarani A (2018) Anchoring Ni (II) on Fe3O4@ tryptophan: a recyclable, green and extremely efficient magnetic nanocatalyst for one‐pot synthesis of 5‐substituted 1H‐tetrazoles and chemoselective oxidation of sulfides and thiols. Organomet Chem 32:e4445
Mohaddeseh S, Nasrollahzadeh M, Ghafuri H, Baran T, Orooji Y, Baran N, Shokouhimehr MR (2022) Modified chitosan-zeolite supported Pd nanoparticles: a reusable catalyst for the synthesis of 5-substituted-1H-tetrazoles from aryl halides. Int J Biol Macromol 209:1573–1585
Mohammadi M, Ghorbani-Choghamarani A, Ramish SM (2023) [ZrFe2O4@ SiO2–N–(TMSP)–ASP–Pd (0)] complex: synthesis, characterizations, and its application as a nanomagnetic catalyst in cross-coupling and click reactions. J Mol Struct 1292:136115
Molaei S, Ghadermazi M (2023a) Mn (II) supported on MCM-41-coated cobalt ferrite as magnetically recyclable catalyst for the one-pot synthesis of 5-substituted 1 H-tetrazoles and selective oxidation of sulfides. Res Chem Intermed 49:5341–5359
Molaei S, Ghadermazi M (2023b) Copper-decorated core–shell structured ordered mesoporous containing cobalt ferrite nanoparticles as high-performance heterogeneous catalyst toward synthesis of tetrazole. Sci Rep 13:15146
Molaei S, Tamoradi T, Ghadermazi M, Ghorbani-Choghamarani A (2019) Ordered mesoporous SBA‐15 functionalized with yttrium (III) and cerium (III) complexes: towards active heterogeneous catalysts for oxidation of sulfides and preparation of 5‐substituted 1H‐tetrazoles. Appl Organomet Chem 33:e4649
Molaei S, Moeini N, Ghadermazi M (2022) Synthesis of CoFe2O4@ amino glycol/Gd nanocomposite as a high-efficiency and reusable nanocatalyst for green oxidation of sulfides and synthesis of 5-substituted 1H-tetrazoles. Appl Organomet Chem 977:122459
Nammalwar B, Muddala NP, Pitchimani R, Bunce RA (2015) OSU-6: a highly efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1 H-tetrazoles. Molecules 20:22757–22766
Ostrovskii VA, Trifonov RE, Popova EA (2012) Medicinal chemistry of tetrazoles. Russ Chem Bull 61:768–780
Parveen M, Ahmad F, Malla AM, Azaz S (2015) SiO2–H3 BO3 promoted solvent-free, green and sustainable synthesis of bioactive 1-substituted-1 H-tetrazole analogues. New J Chem 39:2028–2041
Pirani F, Eshghi H, Rounaghi SA (2023) Immobilized Cu(0) nanoparticles on montmorillonite-modified with benzalkonium chloride (MMT-BAC@Cu(0)): as an eco-friendly and proficient heterogeneous nano-catalyst for green synthesis of 5-substituted 1 H-tetrazoles. RSC Adv 13:6160–6170
Qi G, Dai Y (2010) γ-Fe2O3: a magnetic separable catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide. Chin Chem Lett 21:1029–1032
Safaei-Ghomi J, Paymard-Samani S, Shahbazi-Alavi H (2018) Ultrasonic accelerated efficient synthesis of (1H-tetrazole-5-yl) pyrazines catalyzed by MgFe2O4 nanoparticles as a reusable heterogeneous catalyst. J Nanostruct 8:383–390
Sreedhar B, Suresh Kumar A, Yada D (2011) CuFe2O4 nanoparticles: a magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1H-tetrazoles. Tetrahedron Lett 52:3565–3569
Sun L, Boo WJ, Browning RL, Sue HJ, Clearfield A (2005) Effect of crystallinity on the intercalation of monoamine in α-zirconium phosphate layer structure. Chem Mater 17:5606–5609
Taghavi F, Gholizadeh M, Saljooghi AS, Ramezani M (2017) Cu (ii) immobilized on Fe3O4@APTMS-DFX nanoparticles: an efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles with cytotoxic activity. MedChemComm 8:1953–1964
Teimouri A, Najafi Chermahini A (2011) Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide. Polyhedron 30:2606–2610
Wagner E (1973) Reaction of aluminum azide with cyanoesters. Preparation of tetrazolo [1, 5-c] pyrimidin-5 (6H)-one and tetrazolo [1, 5-c] quinazolin-5 (6H)-one. J Org Chem 38:2976–2981
Wittenberger SJ, Donner BG (1993) Dialkyltin oxide mediated addition of trimethylsilyl azide to nitriles. A novel preparation of 5-substituted tetrazols. J Org Chem 58:4139–4141
Xie A, Cao M, Liu Y, Feng L, Hu X, Dong W (2014) The synthesis of tetrazoles in nanometer aqueous micelles at room temperature. Eur J Org Chem 2:436–441
Xue H, Gau Y, Twamley B, Shreeve JM (2005) New energetic salts based on nitrogen-containing heterocycles. Chem Mater 17:191–198
Yıldız Y, Esirden I, Erken E, Demir E, Kaya M, Şen F (2016) Microwave (Mw)‐assisted synthesis of 5‐substituted 1H‐tetrazoles via [3+2] cycloaddition catalyzed by Mw‐Pd/Co nanoparticles decorated on multi‐walled carbon nanotubes. ChemistrySelect 1:1695–1701
Zekri N, Fareghi-Alamdari R (2016) Spinel ferrites as efficient magnetically reusable nanocatalysts in the solvent-free synthesis of substituted trisphenols. Iran J Catal 6:439–446
Zhu Y, Ren Y, Cai C (2009) One‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl bromides with potassium hexakis (cyano‐κC) ferrate (4−)(K4 [Fe(CN)6]) as cyanide source. Helv Chim Acta 92:171–175
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We are grateful to Malek-Ashtar University of Technology for the financial support of this work.
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Abrishami, F., Daryanavard, M. & Baharvand, S. A Recyclable Heterogeneous Cu/Co/Fe Trimetallic Oxide Nanocatalyst for the Synthesis of 5-Substituted-1H-Tetrazoles. Iran J Sci (2024). https://doi.org/10.1007/s40995-024-01616-w
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DOI: https://doi.org/10.1007/s40995-024-01616-w