5,6-Dihydroxyindole (VIa) and its two mono 0-methyl analogs (VIb, c), and their 2carboxylic acids (XIIJ, tryptamines ( X V ) , and N -acetyltryptamines (XVII) have been synthesized. An improved syntheses of the 5,6-dihydroxyindoles has been developed.The interest in 5,6dihydroxyindole and its 2carboxylic acid is great. They a r e metabolites of the catecholamines and the catecholamine precursors (2), and they undergo enzymatic 0-methylation (3). Furthermore they are the basis of tests for melanomas (4), and a r e the melanin precursors (2). Likewise of wide interest is the study of the metabolism of the ubiquitous serotonin (5hydroxytryptamine), for which 5,6dihydroxytryptamine ( m a ) ( 5 , G ) and Ghydroxymelatonin (7) (Kacetyl-Ghydroxy-5methoxytryptamine) have been reported to be metabolites. w W 0

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o‐Anisidin (I) wurde über das Diazoniumsalz (II) mit den Ketoestern (IIIa), (IIIb) zu dem Hydrazon (IV) kondensiert.