beta-(2-Aminophenyl)-alpha,beta-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 beta-(2-aminophenyl)-alpha,beta-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 beta-(2-aminophenyl)-alpha,beta-ynoates as substrates.

Gold-catalyzed synthesis of dibenzo[1,5]diazocines from β-(2-aminophenyl)-α,β-ynones / Rode, Navnath D.; Arcadi, Antonio; Chiarini, Marco; Marinelli, Fabio; Portalone, Gustavo. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 359:19(2017), pp. 3371-3377. [10.1002/adsc.201700694]

Gold-catalyzed synthesis of dibenzo[1,5]diazocines from β-(2-aminophenyl)-α,β-ynones

PORTALONE, Gustavo
2017

Abstract

beta-(2-Aminophenyl)-alpha,beta-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 beta-(2-aminophenyl)-alpha,beta-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 beta-(2-aminophenyl)-alpha,beta-ynoates as substrates.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1008268
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