Amination of 2-hydroxy- and 2,3-dihydroxynaphthazarins. Synthesis of echinamines A and B, metabolites produced by the sand dollar Scaphechinus mirabilis
- 1 January 2009
- journal article
- Published by Pleiades Publishing Ltd in Russian Journal of Organic Chemistry
- Vol. 45 (1), 37-43
- https://doi.org/10.1134/s1070428009010060
Abstract
2-Hydroxynaphthazarins reacted with aqueous ammonia at the C1=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 C2=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.Keywords
This publication has 8 references indexed in Scilit:
- Synthesis of Echinamines A and B, the First Aminated Hydroxynaphthazarins Produced by the Sea Urchin Scaphechinus mirabilis and Its AnaloguesJournal of Natural Products, 2006
- Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilisTetrahedron Letters, 2006
- Echinamines A and B, First Aminated Hydroxynaphthazarins from the Sea Urchin Scaphechinus mirabilisJournal of Natural Products, 2005
- The Reductive Dehalogenation of Halo-Substituted Naphthazarins and Quinizarins as a Simple Route to Parent CompoundsSynthetic Communications, 1998
- Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivoBioorganic & Medicinal Chemistry Letters, 1998
- Fast evaluation of density functional exchange-correlation terms using the expansion of the electron density in auxiliary basis setsChemical Physics Letters, 1997
- Efficient Synthesis of Aminonaphthoquinones and Azidobenzohydroquinones: Mechanistic Considerations of the Reaction of Hydrazoic Acid with Quinones. An OverviewThe Journal of Organic Chemistry, 1997
- Fluoride salts-alcohols-alumina as reagents for nucleophilic substitution of chlorine atoms for alkoxy groups in 2,3-dichlorosubstituted juglones, naphthazarines, and quinizarinesTetrahedron Letters, 1995