Abstract
1, 9-Diazaanthracene (IV), 4-methyl-1, 9-diazaanthracene (V), 4, 6-phenanthroline (I), 1, 6-phenanthroline (III), and 5-methyl-1, 6-phenanthroline (II) were synthesized by the reaction of 2-, 3-, or 4-aminoquinolines with glycerol or methyl vinyl ketone, in the presence of sulfo-mix, ferrous sulfate, and boric acid. Methylation of I with methyl iodide afforded the monomethiodide (VI) in which methyl iodide was proved to have reacted with the nitrogen in 6-position. Chichibabin amination of I afforded 5-amino-4, 6-phenanthroline (VIII) and this amination was examined by comparison of reaction indices by the Huckel molecular orbital method.
