par Braekman, Jean Claude ;Kaisin, Michel ;Pecher, Jacques
Référence Bulletin des sociétés chimiques belges, 79, page (665-678)
Publication Publié, 1970
Article révisé par les pairs
Résumé : The study of the chromic oxidation of voachalotine (I) shows that the reaction proceeds in two steps. In the first step, (I) is transformed into dehydrovoachalotine (2), voachalotine oxindole (3) and 6‐oxovoachalotine (5). In the second step which occurs in the presence of acetic acid, (2) is further oxidized to dehydrovoachalotine pseudoindoxyl (7), dehydropolyneuridine pseudoindoxyl (6) and dehydrovoachalotine oxindole (8). The structure of each of these compounds is discussed and a scheme for their formation is proposed. The oxidation of voachalotine N‐oxide without added acetic acid gives the same reaction mixture containing (2), (3) and (5). Finally the oxidation of dehydroxymethylvoachalotine (12) in dilute acetic acid gives 6‐oxodehydroxymethylvoachalotine (13). dehydroxymethylpolyneuridine oxindole (14) and dehydroxymethylvoachalotine oxindole (15). No pseudoindoxyl derivatives could be detected in this case. Copyright © 1970 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim