Indole cleavage with mebhydroline by sodium periodate. Part 1: Basic substituted indoles
The reaction behaviour of yohimbine (1), reserpine (5) and mebhydroline (7) as basic substituted indoles against periodate was examined. While 1 and 5 gave only the corresponding amine oxides 2 resp. 6 as definitive products, resulted from 7 beside the N-
Moehrle,Nestle,Westle
p. 741 - 748
(2007/10/03)
Indole cleavage with mebhydroline by sodium periodate: Part 1: Basic substituted indoles
The reaction behaviour of yohimbine (1), reserpine (5) and mebhydroline (7) as basic substituted indoles against periodate was examined. While 1 and 5 gave only the corresponding amine oxides 2 resp. 6 as definitive products, resulted from 7 beside the N-oxide 8 and stepwise dehydrogenation of the tetrahydro-γ-carboline to 9 and 13 also an attack at the indole system. In this ring contractions led to the spiro compounds 10 and 12 and with ring cleavage and loss of a C-1-unit the dilactam 11 was created.