This article describes the synthesis of some novel coumarin compounds to use as acid dyes by using compounds 1 - 4 as starting materials, which were prepared by interaction of 2-hydroxybenzaldehyde with ethyl 3-oxobutanoate, diethylmalonate, 4-nitrobenzenediazonium chloride and 4-sulfobenzenediazonium chloride, respectively. Compound 1 reacted with bromine and 2-cyanoacetohydrazide to give phenacyl bromide derivative 5 and 2-cyanoacetohydrazone derivative 6, respectively. Coupling of compound 6 with equimolar amount of 2-sulfo-4-((4-sulfophenyl) diazenyl)benzenediazonium chloride gave coumarin acid dye 8. Phenacyl bromide derivative 5 re-acted with potassium cyanide in refluxing ethanol to produce compound 7, which on coupling with equimolar amount of 8-hydroxy-6-sulfonaphthalene-2-diazonium chloride and 8-hydroxy-3,6-disulfonaphthalene-1-diazonium chloride gave coumarin acid dyes 9 and 10, respectively. Interaction of compound 2 with 2-amino-5-((4-sulfophenyl)diazenyl)benzenesulfonic acid, benzene-1,4-diamine and 3,3’-dimethoxy-[1,1’-biphenyl]-4,4’-diamine in refluxing ethanol afforded compounds 11, 12 and 14, respectively. Diazonium sulphate of compounds 12 and 14 coupling with 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid gave compounds 13 and 15, respectively. Cyclocondensation of compound 3 with ethyl 3-oxobutanoate, diethyl malonate and malononitrile afforded derivatives of 3-acetyl-2H-chromen-2-one 16, ethyl 2-oxo-2H-chromene-3-carboxylate 17 and 2-imino-2H-chromene-3-carbonitrile 18, respectively. Reaction of sodium benzenesulfonate derivative 4 with ethyl 3-oxobutanoate and hydrazine hydrate gave compounds 19 and 20, respectively. The structures of the newly synthesized compounds were confirmed by elemental analysis, UV/ VIS, IR, 1H NMR and Ms spectral data. The suitability of the prepared dyestuffs for dyeing of wool and silk fabrics has been investigated. The dyed fabric shows good light fastness, very good rubbing, perspiration, washing and excellent sublimation fastness. These dyes have been color shade from blue to violet with very good depth and levelness on fabrics. The dye bath exhaustion and fixation on fabric has been found to be very good.
References
[1]
AL-Adilee, K.J., Abass, A.K. and Taher, A.M. (2016) Synthesis of Some Transition Metal Complexes with New Heterocyclic Thiazolyl Azo Dye and Their Uses as Sensitizers in Photoreactions. Journal of Molecular Structure, 1108, 378-397. http://dx.doi.org/10.1016/j.molstruc.2015.11.038
[2]
Ozkutuk, M., Ipek, E., Aydiner, B., Mamas, S. and Seferoglu, Z. (2016) Synthesis, Spectroscopic, Thermal and Electrochemical Studies on Thiazolyl Azo Based Disperse Dyes Bearing Coumarin. Journal of Molecular Structure, 1108, 521-532. http://dx.doi.org/10.1016/j.molstruc.2015.12.032
[3]
Rufchahi, E.O.M., Gilani, A.G., Taghvaei, V., Karimi, R. and Ramezanzade, N. (2016) Synthesis, Structural Elucidation, Solvatochromism and Spectroscopic Properties of Some Azo Dyes Derived from 6-Chloro-4-hydroxyquino-line-2(1H)-one. Journal of Molecular Structure, 1108, 623-630. http://dx.doi.org/10.1016/j.molstruc.2015.12.001
[4]
Geng, J., Dai, Y., Qian, H., Wang, N. and Huang, W. (2015) 2-Amino-4-chloro-5-formylthiophene-3-carbonitrile Derived Azo Dyes. Dyes and Pigments, 117, 133-140. http://dx.doi.org/10.1016/j.dyepig.2015.02.010
[5]
Megarajan, S., Ahmed, K.B.A., Reddy, G.R.K., Kumar, P.S. and Anbazhagan, V. (2016) Phytoproteins in Green Leaves as Building Blocks for Photosynthesis of Gold Nanoparticles: An Efficient Electrocatalyst towards the Oxidation of Ascorbic Acid and the Reduction of Hydrogen Peroxide. Journal of Photochemistry and Photobiology B: Biology, 155, 7-12. http://dx.doi.org/10.1016/j.jphotobiol.2015.12.009
[6]
Raposo, M.M., Castro, M.C., Belsley, M. and Fonseca, A.M. (2011) Push-Pull Bithiophene Azo-Chromophores Bearing Thiazole and Benzothiazole Acceptor Moieties: Synthesis and Evaluation of Their Redox and Nonlinear Optical Properties. Dyes and Pigments, 91, 454-465. http://dx.doi.org/10.1016/j.dyepig.2011.05.007
[7]
Kaur, N., Dhaka, G. and Singh, J. (2015) Simple Naked-Eye Ratiometric and Colorimetric Receptor for Anions Based on Azo Dye Featuring with Benzimidazole Unit. Tetrahedron Letters, 56, 1162-1165. http://dx.doi.org/10.1016/j.tetlet.2015.01.128
[8]
Kaur, N. and Kumar, S. (2011) Colorimetric Metal Ion Sensors. Tetrahedron, 67, 9233-9264. http://dx.doi.org/10.1016/j.tet.2011.09.003
[9]
Patel, D.R., Patel, N.B., Patel, B.M. and Patel, K.C. (2014) Synthesis and Dyeing Properties of Some New Monoazo Disperse Dyes Derived from 2-Amino-4-(2’,4’-dichlorophenyl)-1,3 Thiazole. Journal of Saudi Chemical Society, 18, 902-913. http://dx.doi.org/10.1016/j.jscs.2011.11.012
[10]
Mohammadi, A., Khalili, B. and Tahavor, M. (2015) Novel Push-Pull Heterocyclic Azo Disperse Dyes Containing Piperazine Moiety: Synthesis, Spectral Properties, Antioxidant Activity and Dyeing Performance on Polyester Fibers. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 150, 799-805. http://dx.doi.org/10.1016/j.saa.2015.06.024
[11]
Saylam, A., Seferoglu, Z. and Ertan, N. (2014) Azo-8-hydroxyquinoline Dyes: The Synthesis, Characterizations and Determination of Tautomeric Properties of Some New Phenyl-and Heteroarylazo-8-hydroxyquinolines. Journal of Molecular Liquids, 195, 267-276. http://dx.doi.org/10.1016/j.molliq.2014.02.027
[12]
Sahoo, J., Mekap, S.K. and Kumar, P.S. (2015) Synthesis, Spectral Characterization of Some New 3-Heteroaryl Azo 4-Hydroxy Coumarin Derivatives and Their Antimicrobial Evaluation. Journal of Taibah University for Science, 9, 187-195. http://dx.doi.org/10.1016/j.jtusci.2014.08.001
[13]
Sunanda, B.P., Krishna, J.J. and Ganapati, S.S. (2013) Greener Protocol for One Pot Synthesis of Coumarin Styryl Dyes. Dyes and Pigments, 97, 105-112. http://dx.doi.org/10.1016/j.dyepig.2012.12.001
[14]
Maryam, A. and Farahnaz, N. (2015) Producing Fluorescent Digital Printing Ink: Investigating the Effect of Type and Amount of Coumarin Derivative Dyes on the Quality of Ink. Journal of Luminescence, 167, 254-260. http://dx.doi.org/10.1016/j.jlumin.2015.06.042
[15]
Simon, B., Azzam, C., Miroslav, M., Danie, T.G. and Denis, J. (2016) Optical Properties of V-Shaped Bis-Coumarins: Ab Initio Insights. Computational and Theoretical Chemistry, 1076, 57-64. http://dx.doi.org/10.1016/j.comptc.2015.12.001
[16]
Anita, K.S., Kailas, K.S. and Ganapati, S.S. (2015) Synthesis and Photophysical Study of Novel Coumarin Based Styryl Dyes. Dyes and Pigments, 120, 190-199. http://dx.doi.org/10.1016/j.dyepig.2015.04.018
[17]
Krishnaiah, V., Rajesh, K.K., Karnewar, S., Rajeswar, R.V., Srigiridhar, K. and Murali, K.T. (2015) Synthesis, Biological Activity Evaluation and Molecular Docking Studies of Novel Coumarin Substituted Thiazolyl-3-aryl-pyrazole-4-carbaldehydes. Bioorganic & Medicinal Chemistry Letters, 25, 5797-5803. http://dx.doi.org/10.1016/j.bmcl.2015.10.042
[18]
Mahmoud, A.A. and Ali, E. (2015) Bismuth Triflate: A Highly Efficient Catalyst for the Synthesis of Bio-Active Coumarin Compounds via One-Pot Multi-Component Reaction. Chinese Journal of Catalysis, 36, 1124-1130. http://dx.doi.org/10.1016/S1872-2067(14)60308-9
[19]
Raghavendra, U.P., Basanagouda, M., Melavanki, R.M., Fattepur, R.H. and Thipperudrappa, J. (2015) Solvatochromic Studies of Biologically Active Iodinated 4-Aryloxymethyl Coumarins and Estimation of Dipole Moments. Journal of Molecular Liquids, 202, 9-16. http://dx.doi.org/10.1016/j.molliq.2014.12.003
[20]
Palita, K., Narid, P., Thitiya, S., Ruangchai, T., Supawadee, N., Taweesak, S., Tinnagon, K., Siriporn, J. and Vinich, P. (2015) N-Coumarin Derivatives as Hole-Transporting Emitters for High Efficiency Solution-Processed Pure Green Electroluminescent Devices. Dyes and Pigments, 112, 227-235. http://dx.doi.org/10.1016/j.dyepig.2014.06.032
[21]
Tolga, E., Mustafa, B. and Meryem, C. (2015) Novel Phthalocyanines Bearing 7-Oxy-3-(3,5-difluorophenyl)coumarin Moieties: Synthesis, Characterization, Photophysical and Photochemical Properties. Journal of Photochemistry and Photobiology A: Chemistry, 300, 6-14. http://dx.doi.org/10.1016/j.jphotochem.2014.12.005
[22]
He, X.W., Shang, Y.J., Zhou, Y., Yu, Z.Y., Han, G., Jin, W.J. and Chen, J.J. (2015) Synthesis of Coumarin-3-carboxylic Esters via FeCl3-Catalyzed Multicomponent Reaction of Salicylaldehydes, Meldrum’s Acid and Alcohols. Tetrahedron, 71, 863-868. http://dx.doi.org/10.1016/j.tet.2014.12.042
[23]
Palita, K., Thitiya, S., Narid, P., Supawadee, N., Tinnagon, K., Siriporn, J., Taweesak, S. and Vinich, P. (2014) Synthesis, Characterization, and Properties of Novel Bis(aryl)carbazole-containing N-Coumarin Derivatives. Tetrahedron Letters, 55, 6689-6693. http://dx.doi.org/10.1016/j.tetlet.2014.10.056
[24]
Mei, M.P., Pushparaj, H., Mani, G., Muthiahpillai, P. and Hyun, T.J. (2014) Solvent Free Synthesis of Coumarin Derivative by the Use of AlSBA-1 Molecular Sieves. Journal of Industrial and Engineering Chemistry, 20, 953-960. http://dx.doi.org/10.1016/j.jiec.2013.06.028
[25]
Margaret, S., Tarik, J.D. and Okenwa, O. (2016) Progress towards Self-Healing Polymers for Composite Structural Applications. Polymer, 83, 260-282. http://dx.doi.org/10.1016/j.polymer.2015.11.008
[26]
Ashis, M., Kotni, S., Ajoy, B. and Sumanta, B. (2014) Role of Charge Transfer Interaction and the Chemical Physics behind Effective Fulleropyrrolidine/Porphyrin Non-Covalent Interaction in Solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 121, 559-568. http://dx.doi.org/10.1016/j.saa.2013.07.054
[27]
Matthew, V.D., Samer, D., Yi, H. and Ulrich, J.K. (2014) Lanthanide Upconversion Nanoparticles and Applications in Bioassays and Bioimaging. Analytica Chimica Acta, 832, 1-33. http://dx.doi.org/10.1016/j.aca.2014.04.030
[28]
Gursoy, A. and Karali, N. (2003) Synthesis, Characterization and Primary Antituberculosis Activity Evaluation of 4-(3-Coumarinyl)-3-benzyl-4-thiazolin-2-one Benzylidenehydrazones. Turkish Journal of Chemistry, 27, 545-551.
[29]
Bhat, M.A., Siddiqui, N. and Khan, S.A. (2008) Synthesis of Novel 3-(4-Acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as Potential Anticonvulsant Agents. Acta Poloniae Pharmaceutica. Drug Research, 65, 235-239.
[30]
Siddiqui, N., Arshad, M.F. and Khan, S.A. (2009) Synthesis of Some New Coumarin Incorporated Thiazolyl Semicarbazones as Anticonvulsants. Acta Poloniae Pharmaceutica, 66, 161-167.
[31]
Gomha, S.M. and Khalil, K.D. (2012)A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity. Molecules, 17, 9335-9347. http://dx.doi.org/10.3390/molecules17089335
[32]
McDonald, R. (1997) Color Physics for Industry. 2nd Edition, Society of Dyes and Colorists, Bradford.
