Some Substituted 1,10-Phenanthrolines¹

Synthesis of a novel pentacycle: 8-Methyl-10-phenylpyrazolo[4′,3′: 5,6]-pyrano[3,2-c]-[1,10]phenanthrolin-7(10H)-one

“…This compound was prepared similarly to a known procedure [7] starting of 8-aminoquinoline (1) (5.02 g, 35 mmol) and diethyl ethoxymethylenemalonate (7.53 g, 35 mmol) to yield 9.56 g (87%) of compound 2 as green-brownish needles; 4-Chloro-1,10-phenanthroline-3-carboxylic acid (5). Compound 4 (573 mg, 2 mmol) was dissolved in DME (30 ml), and aqueous KOH (40%, 30 ml) was added.…”

“…According to [7], the reaction of 8-aminoquinoline (1) with diethyl ethoxymethylenemalonate gave enamine 2, which was cyclized into the phenanthroline derivative 3 in hot diphenyl ether. Subsequent treatment of 3 with thionyl chloride/DMF converted the oxygen function in position 4 into a chlorine substituent (compound 4) [8].…”

Synthesis of Flexible Bis‐Intercalating Ruthenium(II) Complexes

“…Materials Dowex ® 1X8-200 (Cl -form), 1,10-phenanthroline, lithium chloride, 5-chloro-1,10-phenanthroline, aluminium oxide (activated, neutral, Brockman I), potassium hexafluorophosphate, ammonium hexafluorophosphate, anhydrous N,NЈ-dimethylformamide (99.9 %), NaH, KNO 3 [40] 4-Cl-phen was made by the method of Snyder and Freier, [41] dpq was made by the method of Collins et al [17] Tetrachlorocatechol was made by the method of Renner and Hopfer, [42] TRISPHAT was synthesised and resolved by the methods of Favarager et al [43] and [Ru(dpq) 2 Cl 2 ] was synthesised by the method of Anderson et al [44] as for the analogous bpy complex. All general reagents and solvents were used as received (unless specifically stated) and were of analytical reagent grade or higher.…”

A Total Synthesis of Subarine, a Marine Alkaloid Related to the Pyridoacridine Family

“…Compound 7 was prepared as described previously, by action of a mixture of phosphorus oxybromide and phosphorus bromide on the corresponding hydroxy-derivative 6, [10] itself synthesized in 79% yield from 8-aminoquinoline, according to the four-step procedure of Snyder and Freier. [11] The dicarboxylic acid 8 was obtained from 7 by alkaline permanganate oxidation according to the method reported by Wimmer and Wimmer [12] for the preparation of binicotinic acid from phenanthroline. It was then transformed into the corresponding diester 9 by action of DCC and methanol, in 88% yield over the two steps.…”