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.).

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
;
2017-01-01

Abstract

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.).
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/118457
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