COA of Formula: C10H7BrN2On November 3, 1993 ,《Novel applications of vinylogous Mannich reactions. Total synthesis of rugulovasines A and B》 appeared in Journal of the American Chemical Society. The author of the article were Martin, Stephen F.; Liras, Spiros. The article conveys some information:
The total syntheses of the Ergot alkaloids rugulovasines A (I, R = MeNH, R1 = H) and B (R = H, R1 = MeNH) were completed in a concise sequence requiring only eight reactions from com. available 4-bromoindole. The two key steps of the synthesis were the vinylogous Mannich reaction of the iminium salt of II with the furan III and the cyclization of IV by a SRN1 reaction. Thus, 4-bromoindole was converted in a straightforward manner to the 3-acetaldehyde derivative, which after treatment with benzylmethylamine provided the intermediate enamine II. Treatment of II with silyloxyfuran III in the presence of acid produced IV via a vinylogous Mannich reaction. A photostimulated SRN1 reaction of IV was employed to construct the spirocyclic lactone moiety followed by hydrogenolysis gave rugulovasines A and B. The experimental process involved the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2COA of Formula: C10H7BrN2)
2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.COA of Formula: C10H7BrN2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts