Abstract
A series of 6,7-disubstituted 2-hydroxy-3-nitronaphthazarins
were prepared by treatment of 2,3-dichloronaphthazarins with sodium
nitrite. Acid-catalyzed hydrolysis of a mixture of two isomeric
6(7)-ethoxy-7(6)-ethyl-substituted 2-hydroxy-3-nitronaphthazarins
followed by chromatographic separation led to the individually precursors
of echinamines A and B. Further reduction of nitroquinones using
various reducing agents gave echinamines and related 3-amino-2-hydroxynaphthazarins
in good yields.
Key words
5,8-dihydroxy-1,4-naphthoquinones - nucleophilic aromatic
substitution - natural products - echinamine A - echinamine B - sodium nitrite - dichloronaphthazarins
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