Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Some Substituted Formazans and bis Formazans
Corresponding Author(s) : H. Senoz
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
Novel 1-(p-aminophenyl)-3-(p-substituted phenyl)-5-phenylformazan compounds (2a-f) and 1,1'-([1,1'-biphenyl]-4,4'-yl)bis(3-(p-substituted phenyl)-5-phenylformazan compounds (3a-f) were synthesized by diazo coupling reactions of the prepared hydrazones (1a-f) with diazonium salts of phenylenediamine and benzidine, respectively. Novel mono-formazans were obtained with high yields under mild reaction conditions and were crystallized from methanol. Bis-formazans were purified by flash column chromatograph over silica gel. The structures of formazans and bis-formazans were confirmed by elemental analysis, HR-MS and their spectral behaviours were investigated using 1H NMR, 13C NMR, FT-IR techniques. The absorption characteristics of the compounds were examined by UV-visible spectra.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- G. Mariappan, R. Korim, N.M. Joshi, F. Alam, R. Hazarika, D. Kumar and T. Uriah, J. Adv. Pharm. Technol. Res., 1, 396 (2010); doi:10.4103/0110-5558.76438.
- K.G. Desai and K.R. Desai, J. Heterocycl. Chem., 43, 1083 (2006); doi:10.1002/jhet.5570430440.
- M. Kidwai, N. Negi and S.D. Gupta, Chem. Pharm. Bull. (Tokyo), 42, 2363 (1994); doi:10.1248/cpb.42.2363.
- A.N. Babu and R.R. Nadendla, J. Pharm. Res., 4, 983 (2011).
- J.P. Raval, P. R. Patel and P. S. Patel, Int. J. ChemTech Res., 1, 1548 (2009).
- A.B. Samel and N.R. Pai, J. Chem. Pharm. Res., 2, 60 (2010).
- X. Cui, J.Z. Vlahakis, I.E. Crandall and W.A. Szarek, Bioorg. Med. Chem., 16, 1927 (2008); doi:10.1016/j.bmc.2007.11.005.
- J.A. Plumb, R. Milroy and S.B. Kaye, Cancer Res., 49, 4435 (1989).
- C. Henriques, T.L.B. Moreira, C. Maia-Brigagão, A. Henriques-Pons, T.M.U. Carvalho and W. de Souza, Anal. Methods, 3, 2148 (2011); doi:10.1039/c1ay05219e.
- M. Ishiyama, M. Shiga, K. Sasamoto, M. Mizoguchi and P.- He, Chem. Pharm. Bull. (Tokyo), 41, 1118 (1993); doi:10.1248/cpb.41.1118.
- L.C. Edwards, H.S. Freeman and L.D. Claxton, Mutat. Res., 546, 17 (2004); doi:10.1016/j.mrfmmm.2003.10.002.
- M. Szymczyk, W. Czajkowski and R. Stolarski, Dyes Pigments, 42, 227 (1999); doi:10.1016/S0143-7208(99)00033-9.
- H. Tezcan, Spectrochim. Acta A, 69, 971 (2008); doi:10.1016/j.saa.2007.05.061.
- A.A. Abbas, Tetrahedron, 54, 12421 (1998); doi:10.1016/S0040-4020(98)00761-3.
- A.A. Abbas and A.H.M. Elwahy, ARKIVOC, 65 (2009); doi:10.3998/ark.5550190.0010.a07.
- A. Uchiumi and H. Tanaka, Anal. Sci., 5, 425 (1989); doi:10.2116/analsci.5.425.
- G.I. Sigeikin, G.N. Lipunova and I.G. Pervova, Russ. Chem. Rev., 75, 885 (2006); doi:10.1070/RC2006v075n10ABEH003612.
- J.W. Suggitt, G.S. Myers and G.F. Wright, J. Org. Chem., 12, 373 (1947); doi:10.1021/jo01167a003.
- W.F. Ding and X. Jiang, J. Phys. Org. Chem., 11, 809 (1998); doi:10.1002/(SICI)1099-1395(1998110)11:11<809::AID-POC71>3.0.CO;2-1.
- A.R. Katritzky, S.A. Belyakov, D. Cheng and H.D. Durst, Synthesis, 577 (1995); doi:10.1055/s-1995-3958.
- H. Tezcan and N. Özkan, Dyes Pigments, 56, 159 (2003); doi:10.1016/S0143-7208(02)00131-6.
- H. Tezcan and E. Uzluk, Dyes Pigments, 77, 626 (2008); doi:10.1016/j.dyepig.2007.09.003.
- L. Hunter and C.B. Roberts, J. Chem. Soc., 9, 820 (1941); doi:10.1039/jr9410000820.
- O.E. Sherif, Monatsh. Chem., 128, 981 (1997); doi:10.1007/BF00806964.
References
G. Mariappan, R. Korim, N.M. Joshi, F. Alam, R. Hazarika, D. Kumar and T. Uriah, J. Adv. Pharm. Technol. Res., 1, 396 (2010); doi:10.4103/0110-5558.76438.
K.G. Desai and K.R. Desai, J. Heterocycl. Chem., 43, 1083 (2006); doi:10.1002/jhet.5570430440.
M. Kidwai, N. Negi and S.D. Gupta, Chem. Pharm. Bull. (Tokyo), 42, 2363 (1994); doi:10.1248/cpb.42.2363.
A.N. Babu and R.R. Nadendla, J. Pharm. Res., 4, 983 (2011).
J.P. Raval, P. R. Patel and P. S. Patel, Int. J. ChemTech Res., 1, 1548 (2009).
A.B. Samel and N.R. Pai, J. Chem. Pharm. Res., 2, 60 (2010).
X. Cui, J.Z. Vlahakis, I.E. Crandall and W.A. Szarek, Bioorg. Med. Chem., 16, 1927 (2008); doi:10.1016/j.bmc.2007.11.005.
J.A. Plumb, R. Milroy and S.B. Kaye, Cancer Res., 49, 4435 (1989).
C. Henriques, T.L.B. Moreira, C. Maia-Brigagão, A. Henriques-Pons, T.M.U. Carvalho and W. de Souza, Anal. Methods, 3, 2148 (2011); doi:10.1039/c1ay05219e.
M. Ishiyama, M. Shiga, K. Sasamoto, M. Mizoguchi and P.- He, Chem. Pharm. Bull. (Tokyo), 41, 1118 (1993); doi:10.1248/cpb.41.1118.
L.C. Edwards, H.S. Freeman and L.D. Claxton, Mutat. Res., 546, 17 (2004); doi:10.1016/j.mrfmmm.2003.10.002.
M. Szymczyk, W. Czajkowski and R. Stolarski, Dyes Pigments, 42, 227 (1999); doi:10.1016/S0143-7208(99)00033-9.
H. Tezcan, Spectrochim. Acta A, 69, 971 (2008); doi:10.1016/j.saa.2007.05.061.
A.A. Abbas, Tetrahedron, 54, 12421 (1998); doi:10.1016/S0040-4020(98)00761-3.
A.A. Abbas and A.H.M. Elwahy, ARKIVOC, 65 (2009); doi:10.3998/ark.5550190.0010.a07.
A. Uchiumi and H. Tanaka, Anal. Sci., 5, 425 (1989); doi:10.2116/analsci.5.425.
G.I. Sigeikin, G.N. Lipunova and I.G. Pervova, Russ. Chem. Rev., 75, 885 (2006); doi:10.1070/RC2006v075n10ABEH003612.
J.W. Suggitt, G.S. Myers and G.F. Wright, J. Org. Chem., 12, 373 (1947); doi:10.1021/jo01167a003.
W.F. Ding and X. Jiang, J. Phys. Org. Chem., 11, 809 (1998); doi:10.1002/(SICI)1099-1395(1998110)11:11<809::AID-POC71>3.0.CO;2-1.
A.R. Katritzky, S.A. Belyakov, D. Cheng and H.D. Durst, Synthesis, 577 (1995); doi:10.1055/s-1995-3958.
H. Tezcan and N. Özkan, Dyes Pigments, 56, 159 (2003); doi:10.1016/S0143-7208(02)00131-6.
H. Tezcan and E. Uzluk, Dyes Pigments, 77, 626 (2008); doi:10.1016/j.dyepig.2007.09.003.
L. Hunter and C.B. Roberts, J. Chem. Soc., 9, 820 (1941); doi:10.1039/jr9410000820.
O.E. Sherif, Monatsh. Chem., 128, 981 (1997); doi:10.1007/BF00806964.