Synthesis of the Perimidin-4- and -6-one systems
DW Cameron and EL Samuel
Australian Journal of Chemistry
29(11) 2499 - 2509
A simple and efficient method has been devised for the synthesis of π- deficient perimidin-4- and -6-one systems, which were of interest in connection with their reactivity towards nucleophiles. The procedure entails successively, the conversion of substituted naphthalenes into 1,8-dinitro derivatives, reduction to 1,8-diamines, formation of perimidines and dihydroperimidines by treatment with carbonyl compounds, and finally oxidation with Fremy's salt. The course of oxidation was determined by the positions of the other substituents. A number of methyl- and chloro-substituted perimidin-4- and -6-ones have been identified. Oxidation of the intermediate 1,8-diamines produced several new 5- amino-1,4-naphthoquinones as well as 8-amino-1,2-naphthoquinones. Simple derivatives of the latter system have not been previously reported.
Full text doi:10.1071/CH9762499
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