IJOC  Vol.4 No.2 , June 2014
Synthesis of Some New Pyridine-2-yl-Benzylidene-Imines
ABSTRACT
A series of new Schiff bases derived from 2-aminopyridenes and various aromatic aldehydes have been synthesized and thoroughly investigated by 1H and 13C NMR spectroscopy. The imines were found to exist as only a single E-isomer at ambient temperature. Interestingly, 1H- and 13C-NMR chemical shifts of the (CH=N) amino group are affected by the type of substituent group (X) on the aryl ring. Furthermore UV and IR Spectra of some of the title compounds are also reported.

Cite this paper
Alsaygh, A. , Al-Humaidi, J. and Al-Najjar, I. (2014) Synthesis of Some New Pyridine-2-yl-Benzylidene-Imines. International Journal of Organic Chemistry, 4, 116-121. doi: 10.4236/ijoc.2014.42013.
References
[1]   Brodowska, K. and Lodyga-Chruscińska, E. (2014) Schiff Bases—Interesting Range of Applications in Various Fields of Science. Chemik, 68, 129-134.

[2]   Kundariyal, D.S., Patel, P.K. and Bheshdadia, B.M. (2014) Synthesis, Characterization and Biological Activity of 4-Thiazolidinone Derivatives Containing 1H-Pyrazolo[3,4-b]Pyridine Nucleus. Der Chemica Sinica, 5, 138-143.

[3]   Kumar, P.P. and Rani, B.L. (2011) Synthesis and Characterization of New Schiff Bases Containing Pyridine Moiety and Their Derivatives as Antioxidant Agents. International Journal of ChemTech Research, 3, 155-160.

[4]   Bhatia, M.S., Mulani, A.K., Chaudhary, P.B., Ingale, K.B. and Bhatia, N.M. (2009) Synthesis and QSAR Analysis of 5-Substituted (Aryl Methylene) Pyridine-2-Amine Derivatives as Potential Antibacterials. International Journal of Drug Discovery, 1, 1-9.
http://oaji.net/articles/36-1394004826.pdf

[5]   Amr, A.G., Mohamed, A.M., Mohamed, S.F., Abdel-Hafez, N.A. and El-Fotooh G. Hammam, A. (2006) Anticancer Activities of Some Newly Synthesized Pyridine, Pyrane and Pyrimidine Derivatives. Bioorganic & Medicinal Chemistry, 14, 5481-5488.
http://www.sciencedirect.com/science/article/pii/S0968089606003452
http://dx.doi.org/10.1016/j.bmc.2006.04.045


[6]   Jansen, B.A.J., van der Zwan, J., den Dulk, H., Brouwer, J. and Reedijk, J. (2001) Dinuclear Alkyl Diamine Platinum Antitumor Compounds: A Structure-Activity Relationship Study. Journal of Medicinal Chemistry, 44, 245-249.
http://pubs.acs.org/doi/pdf/10.1021/jm0010163

[7]   Hisashi, S., Takao, I., Tetsuya, I., Yuki, K., Hideki, Y. and Itsuo, U. (2000) 4-Aminoquinolines: Novel Nociceptin Antagonists with Analgesic Activity. Journal of Medicinal Chemistry, 43, 4667-4677.
http://dx.doi.org/10.1021/jm0002073

[8]   Věra, K., Martin, S., Waisser, W.K., Milan, P. and Jarmila, K. (1999) New Pyridine Derivatives as Potential Antimicrobial Agents. IlFarmaco, 54, 666-672.
http://dx.doi.org/10.1016/S0014-827X(99)00078-6

[9]   Curtin, D.Y. and Hausser, J.W. (1961) Effects of Structural Changes on the Interconversion of Stereoisomeric Imines, Isoelectronic Models for Vinyl Anions. Journal of the American Chemical Society, 83, 3474-3481.
http://dx.doi.org/10.1021/ja01477a029

[10]   Audoye, P., Coumes, R.-C., Gaset, A. and Gorrichon, J.-P. (1982) Etude structural d’aldiminesderivées des furanne-, thio- phène- et N-méthylpyrrole carboxaldéhydes-2,1-N-hétéroarylidene anilines. Canadian Journal of Chemistry, 60, 1148-1154.
http://www.nrcresearchpress.com/doi/pdf/10.1139/v82-170

[11]   Al-Showiman, S.S., Al-Shalaan, A.M. and Al-Najjar, I.M. (1987) 1H and 13C NMR Studies of Some N-Alkylimines Derived from Thiophenes. The Arab Gulf Journal of Scientific Research, A5, 359-375.

[12]   Al-Showiman, S.S., Al-Najjar, I.M. and Al-Shalaan, A.M. (1987) 1H and 13C NMR Study of Some N-Alkylimines Derived from Furfural and 2-Acetyl Furan. Spectrochimica Acta Part A: Molecular Spectroscopy, 43, 1055-1058.
http://www.sciencedirect.com/science/article/pii/0584853987801782

[13]   Al-Douh, M.H., Al-Fatlawy, A.A. and Abid, O.H. (2004) Synthesis and Characterization of Some 2-(N-Benzoyl- N-Pyrid-2-yl Amino-benzyl)Aminobarbituric Acids via N-Benzylidene Pyridine-2-Amines. Journal of Natural and Applied Sciences, 8, 181-194.
http://www.academia.edu/5199250/

[14]   Dal, H., Süzen, Y. and Sahin, E. (2007) Synthesis, Spectral Studies of Salicylidene-Pyridines: Crystal and Molecular Structure of 2-[(1E)-2-aza-2-(5-Methyl(2-Pyridyl)Ethenyl)]-4-Bromobenzen-1-ol. Spectrochimica Acta Part A: Molecular Spectroscopy, 67, 808-814.
http://www.sciencedirect.com/science/article/pii/S1386142506005130

[15]   Al-Najjar, I.M. and Amin, H.B. (1987) The Carbon-13 Chemical Shifts and the Analysis of the Relaxation Times T1 and Long Range 13C-1H Coupling Constants of Quinoline and of 1-(X-Quinolyl) Ethyl Acetate Derivatives. Spectrochimica Acta Part A: Molecular Spectroscopy, 43, 1307-1315.
http://dx.doi.org/10.1016/S0584-8539(87)80002-8

[16]   Al-Showiman, S.S., Al-Najjar, I.M. and Amin, H.B. (1982) 13C NMR Spectra of Benzo[b]Thiophene and 1-(X-Benzo- [b]Thienyl Acetate Derivatives. Organic Magnetic Resonance, 20, 105-112.
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270200208/

[17]   Ewing, D.F. (1979) 13C Substituent Effects in Monosubstituted Benzenes. Organic Magnetic Resonance, 12, 499-524.
http://dx.doi.org/10.1002/mrc.1270120902

[18]   Arrosmith, J.E., Cook, M.J., Cook, D.J. and Hardsone, D.J. (1978) Long-Range Substituent Induced Chemical Shifts in 13C NMR Spectra of n-Benzylidene Benzyl Amines. Organic Magnetic Resonance, 11, 160-161.
http://dx.doi.org/10.1002/mrc.1270110314

 
 
Top