Preparation of novel imidazo[1,2-a]pyrimidine derived schiff bases at conventional and microwave heating conditions

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In this study, novel imidazo[1,2-a]pyrimidine derived schiff bases were synthesized via imine formation reaction and characterized with various spectral analysis such as FT-IR, 1H NMR, 13C NMR and MS. In addition to conventional heating reactions, microwave-assisted synthesis was applied to the C=N bond formation step. The reactions were carried out at reflux temperature in toluene and magnesium sulfate as drying agent. While final products were obtained at 10-36 h reaction times with moderate to good yields at conventional heating conditions, synthesized at 45-120 min reaction times with good yields at microwave heating conditions. Results showed that microwave-assisted synthesis which is a well-known green process for the synthesizing organic molecules provides to obtain shorter reaction times and higher yields in our study.


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Sruthi, K., Sumakanth, M., Mahendra Kumar, C. B. and Naresh, K., Nitrogen bridged imidazo pyrimidine acetamides: synthesis, molecular docking, toxicity prediction and anti-proliferative studies, European Journal of Biomedical and Pharmaceutical Sciences, 4, 5, 313-320, (2017).

Al-Lami, N., Amer, Z. and Ali, R. A., Preparation, characterization and biological activity of new derivatives of 2-biphenyl-3-aminomethylimidazo(1,2-a)pyrimidine, Journal of Pharmaceutical Sciences and Research, 10, 12, 3344-3350, (2018).

Mantipallya, M., Gangireddya, M. R., Gundlaa, R., Badavath, V. N., Mandhaa, S. R. and Maddipatia, V. C., Rational design, molecular docking and synthesis of novel homopiperazine linked imidazo[1,2-a]pyrimidine derivatives as potent cytotoxic and antimicrobial agents, Bioorganic & Medicinal Chemistry Letters, 29, 2248-2253, (2019).

Goel, R., Luxami V. and Paul, K., Synthetic approaches and functionalizations of imidazo[1,2-a]pyrimidines: an overview of the decade, RSC Advances, 5, 81608-81637, (2015).

Velázquez-Olvera, S., Salgado-Zamora, H., Velázquez-Ponce, M., Campos-Aldrete, E., Reyes-Arellano, A. and Pérez-González, C., Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives, Chemistry Central Journal, 6, 83, 1-9, (2012).

Brodowska, K. and Łodyga-Chruścıńska, E. Schiff bases-interesting range of applications in various fields of science, Chemik, 68, 2, 129-134, (2014).

Berhanu, A. L., Gaurav, Mohiuddin, I., Malik, A. K., Aulakh, J. S., Kumar, V. and Kim, K., A review of the applications of Schiff bases as optical chemical sensors, Trends in Analytical Chemistry, 116, 74-91, (2019).

Srıdevı, G., Arul Antony, S. and Angayarkanı, R., Schiff base metal complexes as anticancer agents, Asian Journal of Chemistry, 31, 3, 493-504, (2019).

Malik, M. A., Dar, O. A., Gull, P., Wani, M. Y. and Hashmi, A. A., Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy, Medicinal Chemistry Communication, 9, 409-436, (2018).

Zhang, J., Xu L. and Wong, W., Energy materials based on metal Schiff base complexes, Coordination Chemistry Reviews, 355, 180-198, (2018).

Collados, J. F., Toledano, E., Guijarro, D. and Yus, M., Microwave-assisted solvent-free synthesis of enantiomerically pure n-(tert-butylsulfinyl)imines, Journal of Organic Chemistry, 77, 5744-5750, (2012).

Elgemeie, G. H. and Masoud, D. M., Recent trends in microwave assisted synthesis of fluorescent dyes, Pigment & Resin Technology, 45, 6 381-407, (2016).

Karnik, K. S., Sarkate, A. P., Jagtap S. D. and Wakte, P. S., Copper catalyzed ligand free microwave mediated synthesis of α-ketoamides from aromatic ketones, Current Microwave Chemistry, 5, 39-45, (2018).

Dyab, A. K. F. and Sadek, K. U., Microwave assisted one-pot green synthesis of cinnoline derivatives inside natural sporopollenin microcapsules, RSC Advances, 8, 23241-23251, (2018).

Shi, Z. and Zhao, Z. Microwave irradiation synthesis of novel indole triazole Schiff base fluorescent probe for Al3+ ion, Inorganica Chimica Acta, 498, 119135, (2019).

Saadaoui, I., Krichen, F., Salah, B. B., Mansour, R. B., Miled, N., Bougatef, A. and Kossentini, M., Design, synthesis and biological evaluation of Schiff bases of 4-amino-1,2,4-triazole derivatives as potent angiotensin converting enzyme inhibitors and antioxidant activities, Journal of Molecular Structure, 1180, 344-354, (2019).

Canton-Díaz, A. M., Munoz-Flores, B. M., Moggio, I., Arias, E., Turlakov, G., Angel-Mosqueda, C. D., Ramirez-Montesb, P. I. and Jimenez-Perez, V. M., Molecular structures, DFT studies and their photophysical properties in solution and solid state. Microwave-assisted multicomponent synthesis of organotin bearing Schiff bases, Journal of Molecular Structure, 1180, 642-650, (2019).

Nguyen, T. B., Nguyen, L. A., Corbin, M., Retailleau, P., Ermolenko, L. and Al-Mourabit, A., Toward the synthesis of sceptrin and benzosceptrin: solvent effect in stereo- and regioselective [2+2] photodimerization and easy access to the fully substituted benzobutane, European Journal of Organic Chemistry, 5861-5868, (2018).

Kethireddy, S., Eppakayala, L. and Maringanti, T. C., Synthesis and antibacterial activity of novel 5,6,7,8‑tetrahydroimidazo [1,2‑a]pyrimidine‑2‑carbohydrazide derivatives, Chemistry Central Journal, 9, 51, 1-6, (2015).


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