70071-65-7

Usage

Type of Compound

Polycyclic compound

Molecular Structure

Contains two fused benzene rings and a linear arrangement of nitrogen atoms

Classification

Heterocyclic compound

Applications

Medicinal chemistry

Biological Activities

Exhibits anti-inflammatory and anti-tumor properties

Importance

Valuable scaffold for the development of new drug molecules

Synthesis

Requires careful attention to reaction conditions and selectivity due to its intricate structure

Upstream product

• 70071-61-3 N,N'-bis(ethyl cyclohex-1-en-2-yl-carboxylate)-1,2-benzenediamine 
• 4840-68-0 2-hydroxy-1-cyclohexenecarboxylic acid ethyl ester 
• 95-54-5 1,2-diamino-benzene 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Relevant academic research and scientific papers

A Short Synthetic Route to 4,7-Dihalogenated 1,10-Phenanthrolines with Additional Groups in 3,8-Position: Soluble Precursors for Macrocyclic Oligophenanthrolines

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.

Alkylation of Heteroaryl Halides by 2:1 Grignard Reagent/Cu(I) Mixtures.Synthesis of Alkylated Octahydrodibenzophenanhtrolines

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.