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An efficient solvent-free synthesis of 3-acetyl-4-arylquinoline-based enaminones and its derivatives using DMFDMA reagent

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Abstract

A series of 3-substituted-4-arylquinoline derivatives were synthesized using 3-acetyl-4-arylquinoline. The acetyl function of 3-acetyl-4-arylquinoline was successfully converted into its corresponding enaminone using DMFDMA as a reagent which in turn successfully converted into pyrazole, isoxazole, pyrimidine, phenyl aminoprop-2-en-1-one, pyridin-2-yl-amino-prop-2-en-1-one, 2-methylpyridine-3-carboxylate by treating with reagents such as hydrazine, hydroxylamine, guanidine hydrochloride, aniline, 2-amino pyridine, ethyl acetoacetate, respectively, under solvent-free microwave irradiation as well as under the conventional thermal heating processes. All the synthesized compounds were found to be obtained in better yields under the microwave irradiation over the conventional process.

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Acknowledgements

Authors are thankful to the administration, VIT University, Vellore, India, for providing facilities to carry out the research work and also thankful to SIF-Chemistry for providing NMR facility. Authors are thankful to University of Hyderabad Network Resource Centre (UGC-NRC) for HRMS facility and also NMR facilities. Author L. Jyothish Kumar is thankful to the VIT University for providing Research Associateship.

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Correspondence to V. Vijayakumar.

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Kumar, L.J., Vijayakumar, V. An efficient solvent-free synthesis of 3-acetyl-4-arylquinoline-based enaminones and its derivatives using DMFDMA reagent. Chem. Pap. 72, 2001–2012 (2018). https://doi.org/10.1007/s11696-017-0375-5

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  • DOI: https://doi.org/10.1007/s11696-017-0375-5

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