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The preparation of 5-hydroxyindole derivatives by the reaction of benzoquinones with certain enamines was suggested by the work of Nenitzescu who reported that the parent quinone, p-benzoquinone, reacts with ethyl 3-aminocrotonate in boiling acetone to yield ethyl 5-hydroxy-2-methylindole-3-carboxylate. The procedure was largely ignored until the 1950s when interest in melanin-related substances and cognition of serotonin as a 5-hydroxyindole derivative stimulated an exploration of this reaction. Keywords: 5-hydroxyindoles; Nenitzescu reaction; quinone; enamine; heterocyclic systems; imides; active methylene compounds; reactants; temperature; solvent |
