Conversion of Zeolite-X into Various Ion Exchanged Forms and Investigation of their Catalytic Efficiency for the Synthesis of 5- Substituted 1H-tetrazole Derivatives
Keywords:
Green method, 5-substituted 1H-tetrazoles, Zeolite H-X, Aromatic aldehydesAbstract
We have developed lucid protocol for the synthesis of 5- substituted 1H-tetrazole derivatives under various aromatic aldehydes in presence of catalyst Zeolite H- X under solvent free condition. In this method reaction times decreases with many more advantages (like low costs, quantitative yields, without using any organic solvent). We also found derivatives of 5-substituted 1H- tetrazole with good to impressive yields (90–97%). In the present experimentation synthesized zeolite is characterized by using techniques like X-ray diffraction (XRD), scanning electronic microscopy (SEM), and Fourier transform-infrared (FT-IR spectroscopy) and catalyst is separated by simple filtration and washed with appropriate solvents without loss of any catalytic activity.
Downloads
References
Alonen, A., Jansson, J., Kallonen, S., Kiriazis, A., Aitio, O., Finel, M., & Kostiainen, R. (2008). Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan. Bioorganic chemistry, 36(3), 148-155.
Aureggi, V., & Sedelmeier, G. (2007). 1, 3‐Dipolar cycloaddition: click chemistry for the synthesis of 5‐substituted tetrazoles from organoaluminum azides and nitriles. Angewandte Chemie International Edition, 46(44), 8440-8444.
Bai, M., Zhang, J. B., Cao, L. H., Li, Y. P., & Wang, D. Z. (2011). Zinc (II) and cadmium (II) metal complexes with bis (tetrazole) ligands: synthesis and crystal structures. Journal of the Chinese Chemical Society, 58(1), 69-74
Bakherad, M., Doosti, R., Keivanloo, A., Gholizadeh, M., & Jadidi, K. (2017). Rapid, green, and catalyst-free one-pot three-component syntheses of 5-substituted 1H-tetrazoles in magnetized water. Journal of the Iranian Chemical Society, 14(12), 2591-2597.
Bonnamour, J., & Bolm, C. (2009). Iron Salts in the Catalyzed Synthesis of 5‐Substituted 1H‐Tetrazoles. Chemistry–A European Journal, 15(18), 4543-4545.
Crosby, D. C., Lei, X., Gibbs, C. G., McDougall, B. R., Robinson Jr, W. E., & Reinecke, M. G. (2010). Design, synthesis, and biological evaluation of novel hybrid dicaffeoyltartaric/diketo acid and tetrazole-substituted L-chicoric acid analogue inhibitors of human immunodeficiency virus type 1 integrase. Journal of medicinal chemistry, 53(22), 8161-8175.
Damavarapu, R., Klapötke, T. M., Stierstorfer, J., & Tarantik, K. R. (2010). Barium salts of tetrazole derivatives–synthesis and characterization. Propellants, Explosives, Pyrotechnics, 35(4), 395-406.
Demko, Z. P., & Sharpless, K. B. (2001). Preparation of 5-substituted 1 H-tetrazoles from nitriles in water. The Journal of organic chemistry, 66(24), 7945-7950.
Duncia, J. V., Pierce, M. E., & Santella III, J. B. (1991). Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole. The Journal of Organic Chemistry, 56(7), 2395-2400.
Ghodse, S. M., Takale, B. S., Hatvate, N. T., & Telvekar, V. N. (2018). Dual Utility of Heterogeneous Catalyst ZSM‐5 for C–C Cleavage Leading to Nitriles, and for the Synthesis of Hydrazides. ChemistrySelect, 3(16), 4168-4172.
Heravi, M. M., Fazeli, A., Oskooie, H. A., Beheshtiha, Y. S., & Valizadeh, H. (2012). Click synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine, and [bmim] N3 via one-pot, three-component reaction. Synlett, 23(20), 2927-2930.
Herr, R. J. (2002). 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorganic & medicinal chemistry, 10(11), 3379-3393.
Karabanovich, G., Roh, J., Soukup, O., Pávková, I., Pasdiorová, M., Tambor, V., ... & Hrabálek, A. (2015). Tetrazole regioisomers in the development of nitro group-containing antitubercular agents. MedChemComm, 6(1), 174-181.
Khan, K. M., Fatima, I., Saad, S. M., Taha, M., & Voelter, W. (2016). An efficient one-pot protocol for the conversion of benzaldehydes into tetrazole analogs. Tetrahedron Letters, 57(5), 523-524.
Ostrovskii, V. A., Trifonov, R. E., & Popova, E. A. (2012). Medicinal chemistry of tetrazoles. Russian Chemical Bulletin, 61(4), 768-780.
Sangal, S. K., & Kumar, A. (1987). Synthesis of Some New Antifungal Tetrazolyl Sulphides. ChemInform, 18(2), 351.
Sridhar, M., & Mallu, K. K. (2013). R, Jillella R, Godala KR, Beeram CR, Chinthala N. Synthesis, 45, 507.
Tisseh, Z. N., Dabiri, M., Nobahar, M., Khavasi, H. R., & Bazgir, A. (2012). Catalyst-free, aqueous and highly diastereoselective synthesis of new 5-substituted 1H-tetrazoles via a multi-component domino Knoevenagel condensation/1, 3 dipolar cycloaddition reaction. Tetrahedron, 68(6), 1769-1773.
Wittenberger, S. J. (1994). Recent developments in tetrazole chemistry. A review. Organic Preparations and Procedures International, 26(5), 499-531.
Wood, E., Crosby, R. M., Dickerson, S., Frye, S. V., Griffin, R., Hunter, R., ... & Ray, J. (2001). A prodrug approach to the design of cRaf1 kinase inhibitors with improved cellular activity. Anti-cancer drug design, 16(1), 1-6.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Inventum Biologicum: An International Journal of Biological Research
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
