Russian Journal of Organic Chemistry

, Volume 45, Issue 1, pp 37–43 | Cite as

Amination of 2-hydroxy- and 2,3-dihydroxynaphthazarins. Synthesis of echinamines A and B, metabolites produced by the sand dollar Scaphechinus mirabilis

  • G. I. Mel’man (Sopel’nyak)
  • N. P. Mishchenko
  • V. A. Denisenko
  • D. V. Berdyshev
  • V. P. Glazunov
  • V. F. Anufriev
Article

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

Aqueous Ammonia Oxazolone Naphthazarin Sand Dollar Hydrazoic Acid 

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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • G. I. Mel’man (Sopel’nyak)
    • 1
  • N. P. Mishchenko
    • 1
  • V. A. Denisenko
    • 1
  • D. V. Berdyshev
    • 1
  • V. P. Glazunov
    • 1
  • V. F. Anufriev
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far East DivisionRussian Academy of SciencesVladivostokRussia

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