210408-29-0Relevant academic research and scientific papers
Indole cleavage with mebhydroline by sodium periodate - Part 2. Mechanism of the dilactam formation
Moehrle,Rohn,Westle
, p. 391 - 399 (2007/10/03)
The γ-carbolines 1a-d reacted with periodate by loss of one carbon - without available precursors - to the eight-membered dilactams 3a-c and the amino acid 9d. As possible intermediates of an indole cleavage α-aminoketones as models were examined. While the oxidation of chain-formed 13 afforded only a small amount of C-lost amide 23, the cyclic species 24 and 32 gave rise to considerably higher yields of the corresponding lactams 29 and 36. From the benzazepinone 32 with Hg(II)-EDTA the intermediate product 43, containing all genuine C-atoms, was formed, which could quantitatively cleaved by periodate to the lactam 36 and formic acid. This mechanism can be transferred to the reactions of the γ-carbolines 1a-d.
Indole cleavage with mebhydroline by sodium periodate: Part 1: Basic substituted indoles
Moehrle,Nestle,Westle
, p. 445 - 452 (2007/10/03)
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.
Indole cleavage with mebhydroline by sodium periodate. Part 1: Basic substituted indoles
Moehrle,Nestle,Westle
, p. 741 - 748 (2007/10/03)
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-
