Abstract
IT has recently been shown1 that adrenochrome (I, R1 = OH, R2 = H, R3 = Me) is rapidly converted into the isomeric 3 : 5 : 6-trihydroxy-l-methylindole 
(II, R1 = OH, R2 = H, R3 = Me) by the action of zinc acetate in aqueous solution. We have now found that this interesting catalysed oxido-reduction rearrangement is general for compounds of the type (I) and provides a very convenient synthetic route to dihydroxyindoles which are of interest as melanin intermediates.
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HARLEY-MASON, J., BU'LOCK, J. Synthesis of 5:6-Dihydroxyindole Derivatives: an Oxido-reduction Rearrangement Catalysed by Zinc Ions. Nature 166, 1036–1037 (1950). https://doi.org/10.1038/1661036c0
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DOI: https://doi.org/10.1038/1661036c0
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