Abstract
A new benzo[c]phenanthrene ketone has been synthesized through Heck coupling and oxidative photocyclization. The optical properties of the target tetracyclic system were also investigated by UV-visible absorption and photoluminescence spectroscopy and an emission in the visible region was observed. The tetracyclic ketone has been reacted with primary amines in the presence of Lewis acid followed by NaBH4 reduction to provide new polyaromatic secondary amines in good yields and purity. All the synthesized new compounds were identified and characterized through a combination of nuclear magnetic resonance spectroscopy and mass spectrometric methods. The cytotoxic activity of all pure benzo[c]phenanthrene derivatives has been evaluated against Hep-2 cell line using (MTT) colorimetric assay.
Highlights
Small polyaromatic molecules are of large importance due to their rich chemistry,[1] physical properties,[2,3]technological and industrial applications.[1]The benzo[c]phenanthreneskeletonis a versatile key building block toward many large functionalized polycyclic aromatic hydrocarbons as well as helicenes.[4,5,6,7,8]The synthesis of the benzo[c]phenanthrene derivatives is of great importance in organic chemistry
We describe a convenient procedure for the synthesis of a new benzo[c]phenanthrene ketone witch has been used as a suitable key building block to provide new secondary amines
The synthesis of the chiral amines was performed as shown in schemes 1-3.p-bromoacetophenone4 undergo Heck coupling with 2-vinylnaphtalene 5(1.5 equiv.) in the presence of Hermann’s catalyst (1mol%) and sodium acetate in DMA, to produce alkene 6 in 73% yield (Scheme 1).The latter was subjected to photocyclization using a 500 W Hg-vapor lamp, on a 500 mg scale per 1 liter of toluene in the presence of a stoechiometric amount of iodine as an oxidizing agent and excess of propylene oxide as a hydrogen iodide scavenger, to afford the 2-acetylbenzo[c]phenanthrene7in 84% yield, after purification by column chromatography
Summary
Small polyaromatic molecules are of large importance due to their rich chemistry,[1] physical properties,[2,3]technological and industrial applications.[1]The benzo[c]phenanthreneskeletonis a versatile key building block toward many large functionalized polycyclic aromatic hydrocarbons as well as helicenes.[4,5,6,7,8]The synthesis of the benzo[c]phenanthrene derivatives is of great importance in organic chemistry. Benzo[c]phenanthrene, Ketone, Heck coupling, Photocyclization,Amines, Cytotoxic activity.
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