Synthesis of 5-Substituted 2, 9-Dimethyl-1,10-Phenanthroline Dialdehydes and Their Schiff Bases with Sulfur-Containing Amines

Zinia Jaman, Mohammad R. Karim, Tasneem A. Siddiquee, Aminul H. Mirza, Mohamad A. Ali

Chemistry, Faculty of Science, University Brunei Darussalam, Brunei Darussalam, Sudan.
Department of Chemistry, Tennessee State University, Nashville, USA.

DOI: 10.4236/ijoc.2013.33029                

Abstract

Eight new Schiff bases of 5-nitro and 5-bromo-substituted 1,10-phenanthroline-2,9-dicarboxaldehydes with sulfur-containing amines, thiosemicarbazide, S-alkyl/aryl dithiocarbazates and 2-mercaptoaniline have been synthesized and characterized by a variety of spectroscopic methods. The condensation reactions of the dialdehydes with the amines were carried out both in the presence and absence of conc. sulfuric acid. A significant increase in yield of the Schiff bases was observed when the reactions were carried out in the presence of sulfuric acid.

Keywords

5-Nitro-1, 10-Phenanthroline Dialdehyde; 5-Bromo-1, 10-Phenanthroline Dialdehyde; Schiff Bases; S-Alkyl/Aryldithiocarbazates; Thiosemicarbazide

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	P. G. Sammes and G. Yahioglu, “1,10-Phenanthroline: A Versatile Ligand,” Chemical Society Reviews, Vol. 23, No. 5, 1994, pp. 327-334. doi:10.1039/cs9942300327
[2]	R. Sahu, D. S. Thakur and P. Kashyap, “Schiff Base: An Overview of Its Medicinal Chemistry Potential of New Drug Molecules,” International Journal of Pharmaceutical Science and Nanotechnology, Vol. 5, No. 3, 2012, pp. 1757-1764.
[3]	J. P. W. Eggert, U. Lüning and C. Nather, “Synthesis and Functionalisation of 5-Substituted Neocuproine Derivatives,” European Journal of Organic Chemistry, Vol. 2005, No. 6, 2005, pp. 1107-1112. doi:10.1002/ejoc.200400635
[4]	J. Reedijk, “Comprehensive Coordination Chemistry,” In: G. Wilkinson, R. D. Gillard and J. A. McCleverty, Eds., Comprehensive Coordination Chemistry, Pergamon, Oxford, Vol. 2, 1987, p. 73.
[5]	M. Akbar Ali, A. H. Mirza, A. L. Tan, L. K. Wei and P. V. Bernhardt, “The Preparation and Characterization of Seven-Coordinated Tin(IV) Complexes of the 2,6-Diacetylpyridine Schiff Bases of S-Alkyl/Aryl-dithiocarbazates and the X-ray Crystal Structure of the [Sn(dapsme)I2] Complex (dapsme=doubly protonated form of the 2,6-Diacetylpyridine Schiff Bases of S-Methyldithiocarbazate),” Polyhedron, Vol. 23, No. 11, 2004, pp. 2037-2043. doi:10.1016/j.poly.2004.05.010
[6]	M. Arifuzzaman, M. R. Karim, T. A. Siddiquee1, A. H. Mirza and M. A. Ali, ”Synthesis and Characterization of New Schiff Bases Formed by Condensation of 2,9-Phenathroline-1,10-Dialdehyde with Sulfur-Containing Amines” International Journal of Organic Chemistry, Vol. 3, No. 1, 2013, pp. 81-86. doi:10.4236/ijoc.2013.31009
[7]	G. F. Smith and F. W. Cagl Jr., “The Improved Synthesis of 5-Nitro-1,10-Phenanthroline,” Journal Organic Chemistry, Vol. 12, No. 6, 1947, pp. 781-784. doi:10.1021/jo01170a007
[8]	H. Astroem and R. Stroemberg, “Synthesis of New OBAN’s and Further Studies on Positioning of the Catalytic Group,” Organic & Biomolecular Chemistry, Vol. 2, No. 13, 2004, pp. 1901-1907. doi:10.1039/b403652b
[9]	R. C. Blake II, A. R. Pavlov, M. Khosraviani, H. E. Ensley, G. E. Kiefer, H. Yu, X, Li and D. A. Blake, “Novel Monoclonal Antibodies with Specificity for Chelated Uranium(VI): Isolation and Binding Properties,” Bioconjugate Chemistry, Vol. 15, No. 5, 2004, pp. 1125-1136. doi:10.1021/bc049889p
[10]	J. P. W. Eggert and U. Lüning, “Towards A,D-(1,10-Phenanthroline)-Bridged Calix[6]arene Dendrimers,” European Journal of Organic Chemistry, Vol. 2007, No. 36, 2007, pp. 6046-6052. doi:10.1002/ejoc.200700639
[11]	M. T. H. Tarafder, K. B. Chew, K. A. Crouse, A. S. M. Ali, B. M. Yamin and H. K. Fun, “Synthesis and Characterization of Cu(II), Ni(II) and Zn(II) Metal complexes of Bidentate NS Isomeric Schiff Bases Derived from S-Methyldithiocarbazate (SMDTC): Bioactivity of the Bidentate NS Isomeric Schiff bases, Some of Their Cu(II), Ni(II) and Zn(II) Complexes and the X-ray Structure of the Bis[S-methyl-β-N-(2-furylmethyl) Methylenedithiocarbazato]Zinc(II) Complex,” Polyhedron, Vol. 21, No. 27-28, 2002, pp. 2683-2690. doi:10.1016/S0277-5387(02)01285-8
[12]	Mughrabi, et al., “Cytoprotective Effect of Benzyl-N’(indol-3-ylmethylidene)-Hyrazinecarbodithioate against Ethanol-Induced Gastric Mucosal Injury in Rats,” Journal of Pure and Applied Chemistry, Vol. 5, No. 3, 2011, pp. 34-42.