INDOLE CLEAVAGE WITH MEBHYDROLINE BY SODIUM PERIODATE - PART 1 - BASIC SUBSTITUTED INDOLES

The reaction behaviour of yohimbine (1), reserpine (5) and mebhydrolin e (7) as basic substituted indoles against periodate was examined. Whi le 1 and 5 gave only the corresponding amine oxides 2 resp, 6 as defin itive products, resulted from 7 beside the N-oxide 8 and stepwise dehy drogenation of the tetrahydro-gamma-carboline to 9 and 13 also an atta ck at the indole system. In this ring contractions led to the spiro co mpounds 10 and 12 and with ring cleavage and loss of a C-1-unit the di lactam 11 was created.