OXIDATION CHEMISTRY OF 5,6-DIHYDROXY-2-METHYLINDOLE

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 ph ases 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 couplin g of the indole ring at the nuclear positions, whereas the remaining o nes were assigned structures 7-8, marked by methylene bridges between the indole moieties and notably 10, featuring a tetrahydrocyclopentadi indole ring system.