Synthesis of <i>α</i>-Naphthol and 2,4,7-Trimethyl-Quinolin-5-ol by Using Manganese (III) Acetate and Analysis of Its Antimicrobial Properties — Oak Academic Publishing
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Synthesis of <i>α</i>-Naphthol and 2,4,7-Trimethyl-Quinolin-5-ol by Using Manganese (III) Acetate and Analysis of Its Antimicrobial Properties
Department of Chemistry, Faculty of Art and Science, Afyon Kocatepe University, Afyonkarahisar, Turkey
1 Department of Chemistry, Faculty of Art and Science, Afyon Kocatepe University, Afyonkarahisar, Turkey
This study involves the aromatization reactions of some ketone derivatives through Manganese (III) acetate. The ketone derivatives used in the study are α -tetralone (1a), 2,4,7-trimethyl-7,8-dihydro quinolinone (1b). At the end of the aromatization reactions of these ketone derivatives the synthesized structures of α-naphthol (2a), 2,4,7-trimethylquinoline-5-ol (2b) were identified by spectroscopic methods such as IR, 1H-NMR, 13 C-NMR, FAB-MS respectively. Micro-organism types such as Escherichia coli, ATCC 25922, Klepsiella pneumoniae , Staphylococcus aureus NRRL B767 , Salmonella typhimurium NRRLB 4420, Bacillus subtilis NRS 744, Bacillus cereus ATCC 11778, Micrococcus luteus ATCC-9341, Listeria monoaytopenus ATCC-7644 bacteria and yeast fungus Candida albicans were used to study the anti-microbial properties of the synthesized 2b compound. The obtained results have determined that compound number 2b has a good antibacterial impact on Bacillus subtilis (NRS-744).
Curran, D.P. (1988) The Design and Application of Free Radical Chain Reactions in Organic Synthesis. Part I. Synthesis, 6, 417-439. http://dx.doi.org/10.1055/s-1988-27600
Iqbal, J., Bhatia, B. and Nayyar, N.K. (1994) Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds. Chemical Reviews, 94, 519-564. http://dx.doi.org/10.1021/cr00026a008
Fossey, J., Lefort, D. and Sorba, J. (1996) Free Radicals in Organic Chemistry J. Am. Chem. Soc. 1996, 118, 4226. Journal of the American Chemical Society, 118, 10678-10678. http://dx.doi.org/10.1021/ja9654490
Brand-Williams, W., Cuvelier, M.E. and Berset, C.L.W.T. (1995) Use of a Free Radical Method to Evaluate Antioxidant Activity. LWT-Food Science and Technology, 28, 25-30. http://dx.doi.org/10.1016/S0023-6438(95)80008-5
Godula, K. and Sames, D. (2006) CH Bond Functionalization in Complex Organic Synthesis. Science, 312, 67-72. http://dx.doi.org/10.1126/science.1114731
Sibi, M.P. and Porter, N.A. (1999) Enantioselective Free Radical Reactions. Accounts of Chemical Research, 32, 163- 171. http://dx.doi.org/10.1021/ar9600547
Recupero, F. and Punta, C. (2007) Free Radical Functionalization of Organic Compounds Catalyzed by N-Hydroxyphthalimide. Chemical Reviews, 107, 3800-3842. http://dx.doi.org/10.1021/cr040170k
Mondal, M. and Bora, U. (2013) Recent Advances in Manganese (iii) Acetate Mediated Organic Synthesis. RSC Advances, 3, 18716-18754. http://dx.doi.org/10.1039/c3ra42480d
Yan, G., Yang, M. and Wu, X. (2013) Synthetic Applications of Arylboronic Acid via an Aryl Radical Transfer Pathway. Organic and Biomolecular Chemistry, 11, 7999-800. http://dx.doi.org/10.1039/c3ob41851k
Fisher, H.C., Berger, O., Gelat, F. and Montchamp, J.L. (2014) Manganese-Catalyzed and Promoted Reactions of H-Phosphinate Esters. Advanced Synthesis and Catalysis, 356, 1199-1204. http://dx.doi.org/10.1002/adsc.201301157
Chany, A.C., Marx, L.B. and Burton, J.W. (2015) Synthesis of Bicyclic Tetrahydrofurans from Linear Precursors Using Manganese (iii) Acetate. Organic and Biomolecular Chemistry, 13, 9190-9193. http://dx.doi.org/10.1039/C5OB01091H
Li, P., Zhao, J., Xia, C. and Li, F. (2014) Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides. Organic Letters, 16, 5992-5995. http://dx.doi.org/10.1021/ol503009f
Matsumoto, R. and Nishino, H. (2015) Advanced Synthesis of Dihydrofurans: Effect of Formic Acid on the Mn (III)- Based Oxidation. Synthetic Communications, 45, 1807-1816. http://dx.doi.org/10.1080/00397911.2015.1049618
Alagoz, O., Yilmaz, M., Pekel, A.T., Graiff, C. and Maggi, R. (2014) Synthesis of Dihydrofuro- and C-Alkenylated Naphthoquinones Catalyzed by Manganese (III) Acetate. RSC Advances, 4, 14644-14654. http://dx.doi.org/10.1039/c3ra48015a
Dey, S.K. and Mukherjee, A. (2014) Manganese (III) Acetate Mediated Catalytic Oxidation of Substituted Dioxolene and Phenols. Journal of Molecular Catalysis A: Chemical, 395, 186-194. http://dx.doi.org/10.1016/j.molcata.2014.08.014
Montchamp, J.L. (2014) Carbon-Hydrogen to Carbon-Phosphorus Transformations. In: Phosphorus Chemistry II, Springer International Publishing, 217-252. http://dx.doi.org/10.1007/128_2014_558
Bicer, E. and Yilmaz, M. (2013) Synthesis of Trifluoromethylated Dihydrofurans by Addition of 1, 3-Dicarbonyl Compounds to Alkenes Promoted by Manganese (III) Acetate. Arkivoc, 3, 304-316.
Bicer, E., Yilmaz, M., Karatas, M. and Pekel, A.T. (2012) Radical Cyclization Reactions via Manganese (III) Acetate Leading to 2-Thienyl-Substituted Dihydrofuran Compounds. Helvetica Chimica Acta, 95, 795-804. http://dx.doi.org/10.1002/hlca.201100397
Biermann, U., Linker, U. and Metzger, J.O. (2013) Manganese (III) Acetate Induced Radical Addition of Azide to Unsaturated Fatty Compounds. European Journal of Lipid Science and Technology, 115, 94-100. http://dx.doi.org/10.1002/ejlt.201200228
Bouhlel, A., Curti, C., Tabele, C. and Vanelle, P. (2013) Manganese (III) Acetate-Mediated Oxidative Cyclization of a-Methylstyrene and Trans-Stilbene with β-Ketosulfones. Molecules, 18, 4293-4307. http://dx.doi.org/10.3390/molecules18044293
Williams, W., Dunk, T., Landerkin, K., Smith, E., White, V., Salomon, J. and Reuben, J. (2005) Accuracy of Identification in BD Phoenix? Using the New Low Inoculum Mode. As presented at the 105th General Meeting of the American Society for Microbiology. https://www.bd.com/ds/technicalCenter/whitepapers/lr884.pdf
Bauer, A.W., Kirby, W.M.M., Sherris, J.C. and Turck, M. (1966) Antibiotic Susceptibility Testing by a Standardized Single Disk Method. American Journal of Clinical Pathology, 45, 493.
Uysal Akkus, G., Al, E. and Korcan, S.E. (2015) Selective Extraction of Toxic Heavy Metals and Biological Activity Studies Using Pyrimidylthioamide Functionalised Calix[4]arene. Supramolecular Chemistry, 27, 522-526. http://dx.doi.org/10.1080/10610278.2015.1020944
Yuan, W., Wei, Y. and Shi, M. (2011) Manganese (III)-Mediated Oxidative Annulation of Vinylidenecyclopropanes with 1,3-Dicarbonyl Compounds. Tetrahedron, 67, 7139-7142. http://dx.doi.org/10.1016/j.tet.2011.06.109
Lopchuk, J.M., Montgomery, W.L., Jasinski, J.P., Gorjifard, S. and Gribble, G.W. (2013) Manganese (III)-Mediated Oxidative Radical Addition of Malonates to 2-Cyanoindoles. Tetrahedron Letters, 54, 6142-6145. http://dx.doi.org/10.1016/j.tetlet.2013.09.012
Demir, A.S., Findik, H., Saygili, N. and Subasi, T.N. (2010) Manganese (III) Acetate-Mediated Synthesis of Biaryls under Microwave Irradiation. Tetrahedron, 66, 1308-1312. http://dx.doi.org/10.1016/j.tet.2009.12.018
Yilmaz, M. and Pekel, A.T. (2005) Manganese (III) Acetate Mediated Synthesis of 3-Trifluoroacetyl-4, 5-Dihydrofurans and 3-(Dihydrofuran-2(3H)-ylidene)-1,1,1-trifluoroacetones by Free Radical Cyclization. Part 1. Journal of Fluorine Chemistry, 126, 401-406. http://dx.doi.org/10.1016/j.jfluchem.2005.02.002
Haque, M.A. and Nishino, H. (2012) Facile Access to 3-Alkyl-Substituted 3-Hydroperoxy-2,4-pyrrolidinediones Using Manganese (III)-Catalyzed Aerobic Oxidation. Synthetic Communications, 42, 608-619. http://dx.doi.org/10.1080/00397911.2010.528129
Demir, A.S. and Findik, H. (2008) Potassium Permanganate/Carboxylic Acid/Organic Solvent: A Powerful Reagent for Enone Oxidation and Aryl Coupling Reactions. Tetrahedron, 64, 6196-6201. http://dx.doi.org/10.1016/j.tet.2008.05.004