70071-61-3Relevant academic research and scientific papers
Alkylation of Heteroaryl Halides by 2:1 Grignard Reagent/Cu(I) Mixtures.Synthesis of Alkylated Octahydrodibenzophenanhtrolines
Bell, Thomas W.,Hu, Lain-Yen,Patel, Sanjay V.
, p. 3847 - 3850 (1987)
Treatment of 2-bromopyridine,3-bromopyridine,2-chloroquinoline,and 5,8-dichloro-1,2,3,4,9,10,11,12-octahydrodibenzophenanthroline(2) with a fourfold excess of 2:1 Grignard reagent/Cu(I) salt mixtures gives alkylated products in 50-85percent yield.Thus prepared are 2-methylpyridine,2-tert-butylpyridine,3-tert-butylpyridine,2-methylquinoline,2-ethylquinoline,2-tert-butylquinoline, and the dimethyl- and di-tert-butylphenanthrolines(3a) and (3b).Full experimental details are provided for the two phenanthrolines, which are prepared in four steps from o-phenylenediamine and ethyl 1-oxocyclohexane-2-carboxylate in 25-30percent overall yield.
A Short Synthetic Route to 4,7-Dihalogenated 1,10-Phenanthrolines with Additional Groups in 3,8-Position: Soluble Precursors for Macrocyclic Oligophenanthrolines
Schmittel, Michael,Ammon, Horst
, p. 785 - 792 (2007/10/03)
A short and efficient preparation of 3,8-dialkylated or 3,8-diarylated 1,10-phenanthrolines-4,7-diones is described. Their chlorination or bromination furnishes the corresponding, highly soluble 4,7-dichloro- or 4,7-dibromo phenanthrolines that constitute versatile precursors to macrocyclic oligophenanthrolines with exo-coordination sites. They can be further reacted by nucleophilic aromatic substitution or Heck-coupling reactions.
