AN IMPROVED SYNTHESIS OF 2-(PYRID-2΄-YL)-1,10-PHENANTHROLINE TRIDENTATE TERPYRIDYL LIGAND

ZIBASERESHT R.¹, KARIMI P.², MOHIT-AZAR S.³, AMIRLOO M.R.⁴, AZIMI M.^5
1Biomaterial Laboratory, Department of Toxicology, Faculty of Medicine, AJA University of Medical Sciences, Tehran, Iran.
²Department of Chemistry, Faculty of Sciences, Islamic Azad University- Tehran North Branch, Tehran, Iran.
³Department of Chemistry, Faculty of Modern Sciences and Technologies, Islamic Azad University- Pharmaceutical Sciences Branch, Tehran, Iran.
⁴Biomaterial Laboratory, Department of Toxicology, Faculty of Medicine, AJA University of Medical Sciences, Tehran, Iran.
⁵Biomaterial Laboratory, Department of Toxicology, Faculty of Medicine, AJA University of Medical Sciences, Tehran, Iran.

Received : 28-11-2013     Accepted : 26-12-2013     Published : 31-12-2013
Volume : 5     Issue : 1       Pages : 153 - 158
Int J Chem Res 5.1 (2013):153-158
DOI : http://dx.doi.org/10.9735/0975-3699.5.1.153-158

Keywords : 2-(pyrid-2΄-yl)-1,10-phenanthroline, synthesis, Skraup, Friedländer
Conflict of Interest : None declared
Acknowledgements/Funding : The authors are grateful to Dr. M.H. Lashkari, Dr. A. Khoshdel, Dr. Sh. Iravani, Dr. S.J. Hosseini Shokouh and Dr. B. Dormanesh for their generous support. The authors are also indebted to Dr. F. Kobarfard of Shahid Beheshti University of Medical Sciences

An improved multistep synthetic route for preparation of a tridentate terpyridyl ligand, 2-(pyrid-2΄-yl)-1,10-phenanthroline, has been reported. In the first step, a Skraup quinoline synthesis using m-toluidine and glycerol was employed. The mixture of 5- and 7-methylquinoline which was obtained was selectively nitrated at 8-carbon position of the 7- derivative. The methyl group in 7-methyl-8-nitroquinoline was then oxidized to an aldehyde followed by a reduction of the nitro group to an amine group. The last step involved a Friedländer condensation of the amino aldehyde with 2-acetylpyridine to obtain the final product with overall high yield. All products were fully characterized.

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