Evidence for the intermediacy of quinone-methides in the rearrangement of aminochromes to 5,6-dihydroxyindoles

Article abstract of DOI:10.1016/S0040-4039(00)98038-9

Oxidation of α-methyldopa methyl ester leads to the aminochrome 4, which, at neutral pH, spontaneously rearranges to give a relatively stable quinone-methide identified as 5. This provides the first evidence for the postulated intermediacy of quinone-methides in the conversion of aminochromes to 5,6-dihydroxyindoles.