b-(2-Aminophenyl)-a,b-ynones afforded exclusively challenging dibenzo[1,5]diazocines by means of (JonPhosAuNCMe)SbF6 catalysis. 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. (Figure presented.).
|Titolo:||Gold-Catalyzed Synthesis of Dibenzo[1,5]diazocines from b-(2-Aminophenyl)-a,b-ynones|
RODE, NAVNATH DNYANESHWAR [Membro del Collaboration Group]
ARCADI, Antonio [Membro del Collaboration Group]
CHIARINI, MARCO [Membro del Collaboration Group]
MARINELLI, Fabio [Writing – Original Draft Preparation] (Corresponding)
|Data di pubblicazione:||2017|
|Appare nelle tipologie:||1.1 Articolo in rivista|