22146-36-7Relevant academic research and scientific papers
Synthesis and characterization of 2,7-bis(2-pyridyl)-1,8-diazaanthraquinone - A redox-active ligand designed for the construction of supramolecular grids
Jain, Rajsapan,Caldwell, Sharon L.,Louie, Anika S.,Hicks, Robin G.
, p. 1263 - 1267 (2006)
Double condensation of 2-acetylpyridine with 1,3-diaminobenzene-4,6- dicarboxaldehyde affords 2,7-bis(2-pyridyl)-1,8-diazaanthracene, which was subsequently oxidized to the corresponding quinone. Electrochemical studies indicate two reversible reduction processes corresponding to semiquinone and hydroquinonate formation. Electron-withdrawing pyridine groups and the nitrogen atoms make this somewhat more easily reduced than anthraquinone. This compound is redox-active and can be reduced to its radical anion, a potential spin-bearing ligand for the construction of [2 x 2] metallo-grid structures.
Synthesis and Reactions of Some Pyridoquinolines (1,8-Diazaanthracenes)
Quast, Helmut,Schoen, Norbert
, p. 133 - 146 (2007/10/02)
The pyridoquinolines 1b, c, and e are synthesized for the first time directly by Friedlaender condensation from 4,6-diaminoisophthalic aldehyde (6) and ketones.Copper(I)-catalyzed decarboxylation of the 2,8-dicarboxylic acid 1e occurs in diethylene glycol monoethyl ether at temperatures as low as 165 deg C affording the parent compound 1a in high yield.Despite steric hindrance by a tert-butyl group methyllithium adds to position 2 of the 2,8-di-tert-butyl compound 1c producing the 1,2-dihydropyridoquinoline 9.Dehydrogenation of the octahydroquinoacridine 7 using palladium on carbon at 250 deg C yields the 1,2,3,4,7,12-hexahydro- (10) and the 5,14-dihydroquinoacridine (11).
