b-(2-Aminophenyl)-a,b-ynones afforded exclusively challenging dibenzo[1,5]diazocines by means of (JonPhosAuNCMe)SbF6catalysis. In contrast with the known gold-catalyzed reaction path of 2-alkynylanilines that leads to indoles, ynones underwent an auto intermolecular hydroamination. This process resulted finally in the formation of an eight-membered ring, likely through a selective 8-exo-dig intramolecular hydroamination that prevailed over the possible cyclocondensation reaction (that would result in the formation of 4-aminoquinoline derivatives). The easy availability of b-(2-aminophenyl)-a,b-ynones and the simple cyclization procedure make this approach suitable for the preparation of a wide range of useful dibenzodiazocines. The methodology can be extended to the use of b-(2-aminophenyl)-a,b-ynoates as substrates.
Gold-Catalyzed Synthesis of Dibenzo[1,5]diazocines from b-(2-Aminophenyl)-a,b-ynones
CHIARINI, MARCO;
2017-01-01
Abstract
b-(2-Aminophenyl)-a,b-ynones afforded exclusively challenging dibenzo[1,5]diazocines by means of (JonPhosAuNCMe)SbF6catalysis. In contrast with the known gold-catalyzed reaction path of 2-alkynylanilines that leads to indoles, ynones underwent an auto intermolecular hydroamination. This process resulted finally in the formation of an eight-membered ring, likely through a selective 8-exo-dig intramolecular hydroamination that prevailed over the possible cyclocondensation reaction (that would result in the formation of 4-aminoquinoline derivatives). The easy availability of b-(2-aminophenyl)-a,b-ynones and the simple cyclization procedure make this approach suitable for the preparation of a wide range of useful dibenzodiazocines. The methodology can be extended to the use of b-(2-aminophenyl)-a,b-ynoates as substrates.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
