A. Napolitano, M. d’Ischia, G. Prota
1988
Citations
0
Influential Citations
30
Citations
Journal
Tetrahedron
Abstract
Abstract In aqueous buffer, at physiological pHs, 5-hydroxyindole ( 3 ) is rapidly oxidised by the H2O2/horseradish peroxidase system to give a complex mixture of oligomeric products, five of which could be isolated after acetylation, and identified as the diacetoxybiindolyls 4 and 5 , and the trimers 6 , 7 and 8 . A similar pattern of products was obtained from the reaction of 3 with other oxidising agents, e.g. potassium ferricyanide, ammonium persulphate and sodium periodate. The Observed reactivity suggests that oxidation of 3 proceeds probably through the intermediacy of the labile quinone Inline 9 . This could be trapped In the form of the adduct 12 when 3 was oxidised with o-chloranil in dry ether.