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Copper-Catalyzed Dihydroquinolinone Synthesis from Isocyanides and O-Benzoyl Hydroxylamines

Author:
Yang, Zhen, Jiang, Kun, Chen, Ying-Chun, Wei, Ye
Source:
Journal of organic chemistry 2019 v.84 no.6 pp. 3725-3734
ISSN:
1520-6904
Subject:
Lewis bases, chemical bonding, chemical reactions, chemical structure, organic chemistry, organic compounds
Abstract:
A copper-catalyzed protocol has been realized for the rapid assembly of dihydroquinolinones from readily accessible isocyanides and O-benzoyl hydroxylamines. The reactions (10 mol % of CuOAc, 10 mol % of dppe, 3 equiv of PhONa, 30 °C) deliver various structurally interesting dihydroquinolinones in moderate to good yields (up to 76%). The reactions may proceed in a cascade manner involving isocyanide insertion into the N–O bond, Mumm-type rearrangement, and intramolecular nucleophilic substitution.
Agid:
6326769