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Studies on Heterocyclic Colouring Matters Part III : 7a,14a‐diaza‐7,7a,14,14a‐tetrahydroquino[2,3‐ b ]acridine‐7,14‐diones (5,7a,12,14a‐tetraaza‐7,7a,14,14a‐tetrahydropentacene‐7,14‐diones)
Author(s) -
Altiparmakian Rodolf
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610329
Subject(s) - chemistry , medicinal chemistry , acridine , chromophore , cyclohexane , organic chemistry , stereochemistry
Abstract 2‐Aminopyridines react with diethyl 2,5‐dioxo‐cyclohexane‐1,4‐dicarboxylate (diethyl succinylsuccinate) to give 7a,14a‐diaza‐6,7,7a,13,14,14a‐hexahydroquino‐[2,3‐ b ] acridine‐7,14‐diones (5,7a,1,14a‐tetraaza‐6,7,7a,13,14,14a‐hexahydropentacene‐7,14‐diones), which are aromatized to the title compounds. Oxidation of these with a mixture of sulfuric and nitric acids results in the formation of their respective 6,13‐quinones, also obtained directly from 2‐aminopyridines and diethyl 2,5‐dichloro‐1,4‐benzoquinone‐3,6‐dicarboxylate. The chromophore of the title compounds is compared with that of quinacridones.