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Gold‐Catalyzed Synthesis of Dibenzo[1,5]diazocines from β‐(2‐Aminophenyl)‐α,β‐ynones
Author(s) -
Rode Navnath D.,
Arcadi Antonio,
Chiarini Marco,
Marinelli Fabio,
Portalone Gustavo
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700694
Subject(s) - hydroamination , chemistry , intramolecular force , catalysis , intermolecular force , combinatorial chemistry , ring (chemistry) , reaction conditions , organic chemistry , molecule
β‐(2‐Aminophenyl)‐α,β‐ynones afforded exclusively challenging dibenzo[1,5]diazocines by means of (JonPhosAuNCMe)SbF 6 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 β‐(2‐aminophenyl)‐α,β‐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 β‐(2‐aminophenyl)‐α,β‐ynoates as substrates.