Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

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Abstract
The reactions between aminochromes and thiols have been reinvestigated. In general aminochromes react with thiols to give mixtures of products including: 5,6-dihydroxyindoles; thio-substituted 5,6-dihydroxyindoles (the mercapto residue is now considered to be in the 4-position of the indole nucleus and not the 7-position as previously reported); and relatively unstable addition products formed between the aminochrome and the thiol. The mechanisms by which these compounds are formed are discussed. The characterization of three thio-substituted 5,6-dihydroxyindoles by nuclear magnetic resonance spectroscopy is described. The nuclear magnetic resonance spectra of a number of 5,6-diacetoxyindole derivatives are reported.

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