Copyright (c) 2023 Neelam Yadav, Ravi Kumar, Sarita Sangwan, Sonu Chauhan, Vidhi Dhanda, Reena Rani, Sheetu Devi, Anil Duhan
This work is licensed under a Creative Commons Attribution 4.0 International License.
Ultrasonic Assisted Three Component Synthesis of 3-Cyano-pyridine-2(1H)-ones
Corresponding Author(s) : Neelam Yadav
Asian Journal of Chemistry,
Vol. 35 No. 12 (2023): Vol 35 Issue 12, 2023
Abstract
The requirements of sustainability and the green chemistry principles have prompted organic chemistry researchers to come up with novel methods for the synthesis of organic compounds that require minimum energy consumption and pose lesser environment harm. Ultrasonication of reaction mixtures is one such methodology. High frequency sound waves are known to emit energy that is utilized in product generation. Attempts were made to synthesize 2-pyridone derivatives using ultrasonication assisted method of synthesizing 3-cyano-pyridine-2(1H)-one starting from a three component one pot reaction. The reaction between cyanoacetamide, aromatic ketones and substituted aromatic aldehydes in the presence of NaOH as base yielded 4,6-diaryl-2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives as a result of one-pot multicomponent reaction. The synthesized 4,6-diaryl-2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives were characterized by 1H NMR, 13C NMR, HRMS and FTIR spectra. Ultrasonication has been found to significantly reduce reaction time, enhance reaction rate and yield compared to conventional heating methods.
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A. De la Hoz, A. Diaz-Ortiz and A. Moreno, Chem. Soc. Rev., 34, 164 (2005); https://doi.org/10.1039/B411438H
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B. Banerjee, Ultrason. Sonochem., 35, 1 (2017); https://doi.org/10.1016/j.ultsonch.2016.09.023
G. Mohammadi Ziarani, Z. Kheilkordi and P. Gholamzadeh, Mol. Divers., 24, 771 (2020); https://doi.org/10.1007/s11030-019-09964-1
N.N. Gharat and V.K. Rathod, Ultrasound-Assisted Organic Synthesis, In: Green Sustainable Process for Chemical and Environmental Engineering and Science, Sonochemical Organic Synthesis, Elsevier Chap. 1, pp 1-44 (2020); https://doi.org/10.1016/B978-0-12-819540-6.00001-2
S. Sangwan, N. Yadav, R. Kumar, S. Chauhan, V. Dhanda, P. Walia and A. Duhan, Eur. J. Med. Chem., 232, 114199 (2022); https://doi.org/10.1016/j.ejmech.2022.114199
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K. Schmidt, U. Riese, Z. Li and M. Hamburger, J. Nat. Prod., 66, 378 (2003); https://doi.org/10.1021/np020430y
N.M. Abd EL-Rahman, T.S. Saleh and M.F. Mady, Ultrason. Sonochem., 16, 70 (2009); https://doi.org/10.1016/j.ultsonch.2008.05.001
V. Kumar, A. Sharma, M. Sharma, U.K. Sharma and A.K. Sinha, Tetrahedron, 63, 9718 (2007); https://doi.org/10.1016/j.tet.2007.07.018
K.S. Suslick and G.J. Price, Annu. Rev. Mater. Sci., 29, 295 (1999); https://doi.org/10.1146/annurev.matsci.29.1.295
D.S. Al-Shamary, Z.A. Al-Othman and M.A. Al-Alshaikh, Asian J. Chem., 25, 6569 (2013); https://doi.org/10.14233/ajchem.2013.14364
H. Zang, Q. Su, Y. Mo, B.-W. Cheng and S. Jun, Ultrason. Sonochem., 17, 749 (2010); https://doi.org/10.1016/j.ultsonch.2010.01.015
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