A. Nowok, J.E. Nycz

Institute of Chemistry, University of Silesia, ul. Szkolna 9, 40-006 Katowice, Poland.

Phenanthrolinesare a group of chemical compounds, having two nitrogen atoms in three fusedbenzenerings (Scheme 1). The most interesting group of phenanthrolines are
1,10-phenanthrolines due to their ability to forming complexes with many metals. They are well soluble materials in many organic solvents.

They are used in analytical chemistry or medicine. In form of iron and cobalt complexes they serve as treatments in anticancer therapy. It is said that the strength of these medicine is even about 100 bigger than popular cisplatinum [1].

Although 1,10-phenanthrolines are so popular, synthesis of them is complex. K. Panda et al [2]synthesized 1,10-phenanthroline derivatives with good yields. However other researches were unable to repeat their resultsusingSkraup method [3]. In chemistry literature we can find other multi step reaction leading to 1,10-phenanthroline derivatives [4].

Our researchisfocused on synthesis of 1,10-phenanthroline derivatives within one-step reaction, by Skraup method. We investigated reaction products using GC/MS and NMR methods. The results showed that 1,10-phenanthroline wasn’t present among double Skraupreaction products. We proved, that it is highly difficult to obtain 1,10-phenanthroline using Skraupmethodology.

Scheme 1. Synthesis of 1,10-phenanthrolines by Skraup method.

On our poster we will show the proposition of reaction mechanism between o-phenylenediamine and crotonaldehyde.

References

1.Rosen, G; Caparros, B; Huvos, AG; Kosloff, C; Nirenberg, A; Cacavio, A; Marcove, RC; Lane, JM; Menhta, B; Urban, C; Cancer 49 (1982)1221-1230.

2.K. Panda, I. Siddiqui, P. K. Mahata, H. Ila, H. Junjappa;Synlett3,449–450 (2004).

3.K. J. Shaffer, D. C. Parr, M. Wenzel, G. J. Rowlands, P. G. Plieger;Eur. J. Org. Chem. 6967–6975 (2012).

4.A. F. Larsen, T. Ulven Org. Lett., 13, 3546–3548 (2011).