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Synthesis of 4,7-Dimethylquinoline-2-carboxaldehyde by Condensation Reactions and Formation of Some New 3-Hetarylformazans
Corresponding Author(s) : E. Aydemir
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
A new carboxaldehyde (4,7-dimethylquinoline-2-carboxaldehyde) from the oxidation of 2,4,7-trimethylquinoline with SeO2 and its condensation products (phenyl-, o-carboxyphenyl-, 4-nitrophenyl-, 2,4-dinitrophenylhydrazone, oxime, semicarbazone), respectively, were synthesized in good yields in the first part of the study. Formazyl compounds with a carboxy group (or groups) in the ortho position (s) relative to the formazan chain have pronounced complex-forming ability. On the other hand, there are limited ways of introducing hetaryl groups to the formazan system. Thus, a new series of formazans having heterocyclic moiety at the 3-position of the chain were obtained by coupling of diazotized anthranilic acid or aniline with phenylhydrazone and o-carboxyphenyhydrazone of 4,7-dimethylquinoline-2-carboxaldehyde, respectively and the effect of the substituents to these coupling reactions was investigated. The structure of the newly synthesized compounds was determined and characterized by UV, IR, NMR and MS spectral data and elemental analysis.
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- Y.H. Al-Araji, J.K. Shneine and A.A. Ahmed, Int. J. Res. Pharm. Chem., 5, 41 (2015).
- A.T. Shinde, N.J. Deshmukh, G.D. Kottapalle and S.B. Zangade, J. Pure Appl. Chem. Res., 5, 61 (2016); https://doi.org/10.21776/ub.jpacr.2016.005.02.247.
- H. Senöz, Hacettepe J. Biol. Chem., 40, 293 (2012).
- G. Buemi, F. Zuccarello, P. Venuvanalingam, M. Ramalingam and S.S.C. Ammal, J. Chem. Soc., Faraday Trans., 94, 3313 (1998); https://doi.org/10.1039/A806334F.
- N. Rabjohn, Org. React., 24, 261 (1976); https://doi.org/10.1002/0471264180.or024.04.
- C.J. Pouchert, The Aldrich Library of IR, Aldrich Chemical Company Inc., USA, edn 2 (1975).
- P.Y. Sollenberger and R.B. Martin, The Chemistry of the Amino Group, S. Patai, Interscience Publishers, London, 360 (1970).
- A.J. Bellamy and R.D. Guthrie, J. Chem. Soc., 2788 (1965); https://doi.org/10.1039/jr9650002788.
- D.L. Pavia, G.M. Lampman and G.S. Kriz Jr., Introduction to Spectroscopy, W.B. Saunders Company, Philadelphia (1979).
- N.P. Bednyagina, I.Ya. Postovskii, A.D. Garnovskii and O.A. Osipov, Usp. Khim., 44, 493 (1975); https://doi.org/10.1070/RC1975v044n06ABEH002356.
- G.N. Lipunova, L.I. Sharova, E.P. Darienko, N.P. Bedyagina, G.I. Sigeikin and Yu.I. Aleksandrov, Zh. Obshch. Khim., 53, 178 (1983).
- H. Szymansky and R. Yekin, NMR Band Handbook, Plenum, New York (1968).
- C.J. Pouchert, The Aldrich Library of IR, Aldrich Chemical Company Inc., USA, edn 2 (1983).
- N.A. Klyuev, E.S. Karavaeav, V.G. Zhilnikov and N.P. Bednyagina, Zh. Org. Khim., 7, 1752 (1981).
- E. Aydemir, Ph.D. Thesis, Yildiz Technical University, Istanbul, Turkey (1998)
References
Y.H. Al-Araji, J.K. Shneine and A.A. Ahmed, Int. J. Res. Pharm. Chem., 5, 41 (2015).
A.T. Shinde, N.J. Deshmukh, G.D. Kottapalle and S.B. Zangade, J. Pure Appl. Chem. Res., 5, 61 (2016); https://doi.org/10.21776/ub.jpacr.2016.005.02.247.
H. Senöz, Hacettepe J. Biol. Chem., 40, 293 (2012).
G. Buemi, F. Zuccarello, P. Venuvanalingam, M. Ramalingam and S.S.C. Ammal, J. Chem. Soc., Faraday Trans., 94, 3313 (1998); https://doi.org/10.1039/A806334F.
N. Rabjohn, Org. React., 24, 261 (1976); https://doi.org/10.1002/0471264180.or024.04.
C.J. Pouchert, The Aldrich Library of IR, Aldrich Chemical Company Inc., USA, edn 2 (1975).
P.Y. Sollenberger and R.B. Martin, The Chemistry of the Amino Group, S. Patai, Interscience Publishers, London, 360 (1970).
A.J. Bellamy and R.D. Guthrie, J. Chem. Soc., 2788 (1965); https://doi.org/10.1039/jr9650002788.
D.L. Pavia, G.M. Lampman and G.S. Kriz Jr., Introduction to Spectroscopy, W.B. Saunders Company, Philadelphia (1979).
N.P. Bednyagina, I.Ya. Postovskii, A.D. Garnovskii and O.A. Osipov, Usp. Khim., 44, 493 (1975); https://doi.org/10.1070/RC1975v044n06ABEH002356.
G.N. Lipunova, L.I. Sharova, E.P. Darienko, N.P. Bedyagina, G.I. Sigeikin and Yu.I. Aleksandrov, Zh. Obshch. Khim., 53, 178 (1983).
H. Szymansky and R. Yekin, NMR Band Handbook, Plenum, New York (1968).
C.J. Pouchert, The Aldrich Library of IR, Aldrich Chemical Company Inc., USA, edn 2 (1983).
N.A. Klyuev, E.S. Karavaeav, V.G. Zhilnikov and N.P. Bednyagina, Zh. Org. Khim., 7, 1752 (1981).
E. Aydemir, Ph.D. Thesis, Yildiz Technical University, Istanbul, Turkey (1998)