Optimization of 1,8-Naphthyridine Derivatives Using Ultrasonic Method: Synthesis, Characterization, and Enhanced Properties Study

Authors

  • Dr. Shweta A. Patel
  • Dr. Ami Reepalkumar Patel

Keywords:

Morpholine, Ultrasound irradiation, One pot multi-component reaction, Optimization, aqueous condition

Abstract

The increasing concern for environmental sustainability and the need for efficient and green chemical synthesis have driven the development of alternative methods for producing new compound. Compared to more conventional techniques, ultrasonic irradiation offers improved preparation yields, a quicker reaction time and more comfortable conditions. The use of ultrasound sonication is a green and efficient synthetic method that utilizes sound waves to initiate chemical reactions. We optimized various reaction parameters, such as solvent, temperature, catalyst amount, and reaction time, to identify the best reaction conditions for the synthesis of the derivatives. Using morpholine as a catalyst in an aqueous condition and the ultrasonic irradiation method, ethyl 2-oxo-4-phenyl-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate and its derivatives were synthesized by taking advantages of this. Synthesized compounds were confirmed through IR, 1H NMR, 13C NMR and mass spectra. This method provides us modern green platform to synthesize and optimize ethyl 2-oxo-4-phenyl-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate derivatives.

Downloads

Download data is not yet available.

References

Melchert, W. R., Reis, B. F., & Rocha, F. R. (2012). Green chemistry and the evolution of flow analysis. A review. Analytica Chimica Acta, 714, 8-19.

Lenoir, D., Schramm, K. W., & Lalah, J. O. (2020). Green Chemistry: Some important forerunners and current issues. Sustainable Chemistry and Pharmacy, 18, 100313.

Lebel, H., & Paquet, V. (2002). Highly chemoselective rhodium-catalyzed methylenation of fluorine-containing ketones. Organic letters, 4(10), 1671-1674.

Lin, M. Y., Maddirala, S. J., & Liu, R. S. (2005). Solvent-dependent chemoselectivity in ruthenium-catalyzed cyclization of Iodoalkyne− Epoxide functionalities. Organic Letters, 7(9), 1745-1748.

Wang, X., Xu, X. P., Wang, S. Y., Zhou, W., & Ji, S. J. (2013). Highly efficient chemoselective synthesis of polysubstituted pyrroles via isocyanide-based multicomponent domino reaction. Organic letters, 15(16), 4246-4249.

Cella, R., & Stefani, H. A. (2009). Ultrasound in heterocycles chemistry. Tetrahedron, 65(13), 2619-2641.

Safari, J., Heydarian, M., & Zarnegar, Z. (2017). Synthesis of 2-amino-7-hydroxy-4H-chromene derivatives under ultrasound irradiation: A rapid procedure without catalyst. Arabian Journal of Chemistry, 10, S2994-S3000.

Chen, P., Zhao, Y., Zhang, J., Duan, Y., Dai, J., He, J., ... & Tang, Q. (2022). Design, synthesis and anticancer evaluation of 6, 7-disubstituted-4-phenoxyquinoline derivatives bearing 1, 8-naphthyridine-3-carboxamide moiety as novel multi-target TKIs. Bioorganic Chemistry, 121, 105672.

Ahmed, N. S., AlFooty, K. O., & Khalifah, S. S. (2014). Synthesis of 1, 8-naphthyridine derivatives under ultrasound irradiation and cytotoxic activity against HepG2 cell lines. Journal of Chemistry, 2014.

Fadda, A. A., El-Defrawy, A. M., & El-Hadidy, S. A. (2012). Synthesis, cytotoxicity evaluation, DFT molecular modeling studies and quantitative structure activity relationship of novel 1, 8-naphthyridines. Am J Org Chem, 2(4), 87-96.

Massari, S., Daelemans, D., Barreca, M. L., Knezevich, A., Sabatini, S., Cecchetti, V., ... & Tabarrini, O. (2010). A 1, 8-naphthyridone derivative targets the HIV-1 Tat-mediated transcription and potently inhibits the HIV-1 replication. Journal of medicinal chemistry, 53(2), 641-648.

Ojha, M., Yadav, D., Kumar, A., Dasgupta, S., & Yadav, R. (2021). 1, 8-naphthyridine derivatives: a privileged scaffold for versatile biological activities. Mini Reviews in Medicinal Chemistry, 21(5), 586-601.

Mithula, S., Nandikolla, A., Murugesan, S., & Kondapalli, V. G. (2021). 1, 8-naphthyridine derivatives: An updated review on recent advancements of their myriad biological activities. Future Medicinal Chemistry, 13(18), 1591-1618.

Quintela, J. M., Peinador, C., González, L., Iglesias, R., Paramá, A., Álvarez, F., ... & Riguera, R. (2003). Piperazine N-substituted naphthyridines, pyridothienopyrimidines and pyridothienotriazines: new antiprotozoals active against Philasterides dicentrarchi. European journal of medicinal chemistry, 38(3), 265-275.

Ferrarini, P. L., Mori, C., Badawneh, M., Franconi, F., Manera, C., Miceli, M., & Saccomanni, G. (2000). Synthesis and antiplatelet activity of some 3-phenyl-1, 8-naphthyridine derivatives. Il Farmaco, 55(9-10), 603-610.

Gallinger, T. L., Aboagye, S. Y., Obermann, W., Weiss, M., Grünweller, A., Unverzagt, C., ... & Haeberlein, S. (2022). First in silico screening of insect molecules for identification of novel anti-parasitic compounds. Pharmaceuticals, 15(2), 119.

Additional Files

Published

03-03-2024

How to Cite

Dr. Shweta A. Patel, & Dr. Ami Reepalkumar Patel. (2024). Optimization of 1,8-Naphthyridine Derivatives Using Ultrasonic Method: Synthesis, Characterization, and Enhanced Properties Study. Vidhyayana - An International Multidisciplinary Peer-Reviewed E-Journal - ISSN 2454-8596, 9(si2). Retrieved from http://j.vidhyayanaejournal.org/index.php/journal/article/view/1651