Journal
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 45, Issue 1, Pages 37-43Publisher
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428009010060
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Funding
- Presidium of the Russian Academy of Sciences [02.522.11.2013]
- Far East and Siberian Divisions of the Russian Academy of Sciences [07-II-SO-05-020]
- [06-III-V-05-131]
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2-Hydroxynaphthazarins reacted with aqueous ammonia at the C(1)=O carbonyl group, following the addition-elimination pattern with formation of 8-aminojuglone derivatives. Reactions of 2,3-dihydroxynaphthazarins with the same reagent involved the C(2)=O carbonyl group of the corresponding 1,2-naphthoquinoid tautomer to produce 2-aminonaphthazarin derivatives. 7-Ethyl-2,3,6-trihydroxynaphthazarin (echinochrome) reacted with aqueous ammonia to give 3(2)-amino-7-ethyl-2(3),6-dihydroxynaphthazarins (echinamines A and B) that are metabolites recently isolated from the sand dollar Scaphechinus mirabilis.
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