One-Pot Four Component Reaction for the Synthesis of Formazans in an Environmentally Benign Procedure Mediated by KHSO4

DOI: 10.4236/gsc.2015.53016   PDF   HTML   XML   4,513 Downloads   5,145 Views   Citations


A microwave mediated solvent free one pot synthesis of formazans is developed using the solid acid, KHSO4. The products were obtained in a short reaction time in high yield. This study was undertaken to find an alternative and green method for the synthesis of formazans in the absence of corrosive mineral acids, buffered solutions and volatile organic compounds (VOCs).

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Das, P. and Begum, J. (2015) One-Pot Four Component Reaction for the Synthesis of Formazans in an Environmentally Benign Procedure Mediated by KHSO4. Green and Sustainable Chemistry, 5, 128-135. doi: 10.4236/gsc.2015.53016.

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The authors declare no conflicts of interest.


[1] Pechmann, H. (1892) Ueber die Einwirkung von Diazobenzol auf Malonsaure. Berichte, 25, 3175.
[2] Bamberger, E. and Wheelwright, E.W. (1892) Ueber die Einwirkung von Diazobenzol auf Acetessigather. Berichte, 25, 3201.
[3] Sanli, S., Sanli, N. and Alsancak, G. (2009) Determination of Prootonation Constants of Some Tetracycline Antibiotics by Potentiommetry and LC Methods in Water and Acetinitrile-Water Binary Mixtures. Journal of the Brazilian Chemical Society, 20, 939-946.
[4] Beltran, J.L., Sanli, N., Fonrodona, G., Barren, D., Ozkan, G. and Barbosa, J. (2003) Spectrophotometric, Potentiometric and Chromatographic pKa Values of Polyphenolic Acids in Water and Acetonitrile-Water Media. Analytica Chimica Acta, 484, 253-264.
[5] Senoz, H. (2012) The Chemistry of Formazans and Tetrazolium Salts. Hacettepe Journal of Biology and Chemistry, 40, 293-301.
[6] Tezcan, H. and Ozbek, N. (2005) The Synthesis of Some Bis-Substituted Formazans and the Investigation of the Effect of Substituent upon Their UV-Vis Absorption Values. Communications Faculty of Sciences University of Ankara Series B, 51, 13-28.
[7] Debnam, P.M. and Shearer, G. (1997) Colorimetric Assay for Substrates of NADP+-Dependent Dehydrogenase Based on Reduction of Tetrazolium Dyes to Its Soluble Formazans. Analytical Biochemistry, 250, 253-255.
[8] Barsoum, B.N., Khella, S.K., Elwaby, A.H.M., Abbas, A.A. and Ibrahim, Y.A. (1998) In Evaluation of Some New 14-and 15-Crown Formazans as Carriers in Cesium Ion Selective Electrodes. Talanta, 47, 1215.
[9] Van Aardt, J.H.P., Tadros, W., Cottrell, H.J., Pain, D.L., Slack, R., Brand, J.C.D., Minkoff, G.J., Mulcahy, M.F.R., Watt, I.C., Ward, E.R., Coulson, T.M., Hawkins, J.W., Balenovic, K., Dvornik, D., Blanchard, J.P., Goering, H.L., Lane, E.S. and Williams, C. (1954) Some Heptatriene Derivatives. Journal of the Chemical Society, 2967.
[10] Misra, V.S., Dhar, S. and Chowdhary, B.L. (1978) Synthesis of Some Newer Formazans and Tetrazolium Salts as Antiviral Agents. Pharmazie, 33, 790-792.
[11] Mukherjee, D.D., Shukla, S.K. and Chowdhary, B.L. (1981) Synthesis of Some New Formazans as Potential Anti Viral Agents. Archiv der Pharmazie, 314, 991-994.
[12] Desai, R.M. and Desai, J.M. (1999) Synthesis and Antimicrobial Activity of Some New Formazan Derivatives. Indian Journal of Heterocyclic Chemistry, 8, 329-331.
[13] Samel, A.B. and Pai, N.R. (2010) Synthesis and Antimicrobial Activity of Some Novel Formazan Derivatives. Journal of Chemical and Pharmaceutical Research, 2, 60-67.
[14] Kalsi, R., Pande, K., Bhalla, T.N., Parmar, S.S. and Brathwal, J.P. (1988) Novel Formazans as Potent Anti-Inflammatory and Analgesic Agents. Pharmacology, 37, 218-224.
[15] Desai, K.G. and Desai, K.R. (2006) Microbial Screening of Novel Synthesized Formazans Having Amide Linkagesφ. Journal of Heterocyclic Chemistry, 43, 1083-1089.
[16] Nineham, A.W. (1955) The Chemistry of Formazans and Tetrazolium Salts. Chemical Reviews, 5, 355-483.
[17] Ashley, J.N., Davis, B.M., Nineham, A.W. and Slack, R. (1953) Tetrazolium Compounds. Part I. Tetrazolium Compounds Containing Substituted Phenyl and Heterocyclic Rings. Journal of the Chemical Society, 1953, 3881-3888.
[18] Korzeniowski, S.H. and Gokel, G.W. (1977) Crown Cation Complex Effect. V. Reaction of Aryldiazonium Ions in Non Polar Media. Tetrahedron Letters, 18, 1637-1640.
[19] Tezcan, H. (2008) Synthesis and Spectral Properties of Some Bis-Substituted Formazans. Spectrochimica Acta Part A, 69, 971-979.
[20] Iwamoto, H., Yoshimura, M., Sonoda, T. and Kobayashi, H. (1983) Anion-Catalyzed Phase-Transfer Catalysis. I. Application to Diazo-Coupling Reactions. Bulletin of the Chemical Society of Japan, 56, 796-801.
[21] Hashida, Y., Kubota, K. and Sekiguchi, S. (1988) Phase-Transfer-Catalyzed Azo Coupling Reactions in Two-Phase Systems. Bulletin of the Chemical Society of Japan, 61, 905-909.
[22] Katritzky, A.R., Belyakov, S.A., Cheng, D. and Durst, H.D. (1995) Syntheses of Formazans under Phase-Transfer Conditions. Synthesis, 1995, 577-581.
[23] Tezcan, H. and Uzluk, E. (2007) The Synthesis and Spectral Properties Determination of 1,3-Substituted Phenyl-5- phenylformazans. Dyes and Pigments, 75, 633-640.
[24] Tezcan, H., Uzluk, E. and Aksu, M.L. (2008) Electrochemical and Structural Properties of 1,3-Substituted (-Cl, -Br) Phenyl-5-Phenylformazans. Journal of Electroanalytical Chemistry, 619-620, 105-116.
[25] Tezcan, H., Can, S. and Tezcan, R. (2002) The Synthesis and Spectral Properties Determination of 3-Substituted-1,5- diphenylformazans. Dyes and Pigments, 52, 121-127.
[26] Tezcan, H. and Ozkan, N. (2003) Substituent Effect on the Spectral Properties of Some 3-Substituted Formazans. Dyes and Pigments, 56, 159-166.
[27] Spande, T.F. and Glenner, G. (1973) Reactions of Indole with Diazonium Salts (Fast Red B). Journal of the American Chemical Society, 95, 3400-3402.
[28] Bamoniri, A., Mirjalili, B.B.F. and Arani, N.M. (2014) Nano BF3·SiO2: A Green Heterogeneous Solid Acid for Synthesis of Formazan Dyes under Solvent Free Condition. Journal of Molecular Catalysis A: Chemical, 393, 272-278.
[29] Jin, J., Wen, Z., Long, J., Wang, Y., Matsuura, T. and Meng, J. (2000) One-Pot Diazo Coupling Reaction under Microwave Irradiation in the Absence of Solvents. Synthetic Communications, 30, 829-834.
[30] Das, P.J. and Begum, J. (2015) Microwave Mediated Solvent Free Synthesis of Formazans Catalyzed by Simple Ionic Liquids Derived from Dialkylammonium Salts. RSC Advances, 5, 44604-44609.
[31] Tezcan, H. and Ekmekci, G. (2010) Electrochemical and Spectroscopic Behaviours of 1-(o-, m-, p-Cl or -Br) Substituted Phenyl-3,5-Diphenylformazans in Dimethylsulphoxide. Acta Chimica Slovenica, 57, 189-197.
[32] Furniss, B.S., Hannaford, A.J., Smith, P.W.G. and Tatchell, A.R., Eds. (2007) Vogel’s Textbook of Practical Organic Chemistry. 5th Edition, Pearson Education, London.

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