RING CLEAVAGE AND RING EXPANSION OF INDOLES BY SUPEROXYDE ION

Article abstract of DOI:10.1016/S0040-4039(00)85631-2

The reaction of indoles (1) with superoxide ion resulted in ring cleavage to give o-formyl and o-acylaminoketones (6) or N-acylanthranilic acid (8) and ring expansion yielding 2-quinolones (7).All reactions are chemiluminescent except that of 2-methylindole (1h), which gave a coupled product (9).