In aqueous buffer at neutral pHs. 5,6-dihydroxy-2-methylindole (2) is rapidly oxidised by the peroxidase/H2O2 system to give in the early phases a complex mixture of oligomers, the major of which were isolated as the O-acetyl derivatives. Five of these were formulated as the 3,3′-biindolyl 3, the isomeric dimers 4–6 and trimer 9, arising by coupling of the indole ring at the nuclear positions, whereas the remaining ones were assigned structures 7–8, marked by methylene bridges between the indole moieties, and notably 10, featuring a tetrahydrocyclopentadiindole ring system.
Oxidation chemistry of 5,6-dihydroxy-2-methylindole / Napolitano, Alessandra; Crescenzi, Orlando; K., Tsiakas; Prota, Giuseppe. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 49:40(1993), pp. 9143-9150. [10.1016/S0040-4020(01)91231-1]
Oxidation chemistry of 5,6-dihydroxy-2-methylindole.
NAPOLITANO, ALESSANDRA;CRESCENZI, ORLANDO;PROTA, GIUSEPPE
1993
Abstract
In aqueous buffer at neutral pHs. 5,6-dihydroxy-2-methylindole (2) is rapidly oxidised by the peroxidase/H2O2 system to give in the early phases a complex mixture of oligomers, the major of which were isolated as the O-acetyl derivatives. Five of these were formulated as the 3,3′-biindolyl 3, the isomeric dimers 4–6 and trimer 9, arising by coupling of the indole ring at the nuclear positions, whereas the remaining ones were assigned structures 7–8, marked by methylene bridges between the indole moieties, and notably 10, featuring a tetrahydrocyclopentadiindole ring system.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
