15069-79-1Relevant articles and documents
MUSHROOM TYROSINASE AS AN OXIDANT FOR THE SYNTHESIS OF 5,6-DIHYDROXYINDOLE DERIVATIVES
Lim, Mu-Ill,Patil, Dilip G.
, p. 3775 - 3778 (1987)
Several catecholamines have been converted to 5,6-diacetoxyindole derivatives by the use of mushroom tyrosinase as oxidant.
The first entry to 5,6-dihydroxy-3-mercaptoindole, 5-hydroxy-3-mercaptoindole and their 2-carbomethoxy derivatives by a mild thiocyanation/reduction methodology
Pezzella, Alessandro,Palma, Aniello,Iadonisi, Alfonso,Napolitano, Alessandra,d'Ischia, Marco
, p. 3883 - 3886 (2007)
The hitherto unknown 5,6-dihydroxy-3-mercaptoindole (4a) and its 2-carbomethoxy derivative (4b), as well as the analogous 5-hydroxy 3-mercaptoindoles, have been conveniently obtained as O,S-acetyl derivatives 3a-d by thiocyanation of the corresponding acetoxyindoles 1a-d with the NH4SCN/oxone system followed by SmI2 reduction and acetylation.
New insight into the oxidative chemistry of noradrenaline: Competitive o-quinone cyclisation and chain fission routes leading to an unusual 4-[bis-(1H-5,6-dihydroxyindol-2-yl)methyl]-1,2-dihydroxybenzene derivative
Manini, Paola,Pezzella, Alessandro,Panzella, Lucia,Napolitano, Alessandra,D'Ischia, Marco
, p. 4075 - 4080 (2005)
Oxidation of 5×10-3 M noradrenaline in aqueous phosphate buffer, pH 7.4, with K3Fe(CN)6, NaIO4 or Fe2+/EDTA/H2O2 followed by extraction with ethyl acetate and acetylation with Ac2O/Pyr led to a main reaction product which was isolated and identified as 4-[bis-(1H-5,6-diacetoxyindol-2-yl) methyl]-1,2-diacetoxybenzene, an unprecedented [bis-(indol-2-yl)methyl]-benzene derivative unsubstituted on the 3-position of the indole rings. This product was also obtained in 40% yield by reaction of 5,6-dihydroxyindole with 3,4-dihydroxybenzaldehyde. Other components of the oxidation mixture were 1-acetyl-3,5,6-triacetoxyindole, derived from noradrenolutin, and 5,6-diacetoxyindole, originating from cyclisation/dehydration of the o-quinone of noradrenaline, along with some 3,4-diacetoxybenzaldehyde. Inspection of the aqueous phase revealed the presence of 3,4-dihydroxymandelic acid and 3,4-dihydroxybenzaldehyde, derived from oxidative breakdown of the 2-amino-1-hydroxyethyl chain via a p-quinomethane intermediate. These results disclose new aspects of the oxidative chemistry of noradrenaline beyond the aminochrome stage and provide a route to novel [bis-(indol-2-yl)methyl]-benzene derivatives of potential pharmacological interest.
Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds
Capelli, Luigia,Manini, Paola,Pezzella, Alessandro,Napolitano, Alessandra,D'Ischia, Marco
supporting information; experimental part, p. 7191 - 7194 (2009/12/09)
(Chemical Equation Presented) A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7′-, 2,2′-, and 2,3′-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5