Journal
SYNTHESIS-STUTTGART
Volume -, Issue 20, Pages 3350-3358Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260229
Keywords
5,8-dihydroxy-1,4-naphthoquinones; nucleophilic aromatic substitution; natural products; echinamine A; echinamine B; sodium nitrite; dichloronaphthazarins
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Funding
- International Science and Technology Center [4009]
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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.
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