Unexpected reaction of melatonin derivatives with performic acid

Abstract A series of carbamate melatonin derivatives was treated with performic acid, providing tricyclic products with a 3-hydroxytetrahydropyrrolo[2,3- b ]indole skeleton. An unusual migration of carbamate groups was observed in some cases, and the reaction appeared to be strongly dependent on the type of substituent in the phenyl ring of the phenylcarbamate group. Theoretical calculations suggest that the reaction is kinetically controlled.