21160-02-1Relevant articles and documents
Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines
Wang, Quannan,Lou, Jiang,Huang, Zilong,Yu, Zhengkun
, p. 2083 - 2092 (2019/02/19)
Rhodium(III)-catalyzed annulation of acetophenone O-acetyl oximes with allenoates was achieved, affording isoquinolines in good to excellent yields with high regioselectivities under redox-neutral conditions. Allenoates acted as the C2 synthons in the annulation reaction. The present synthetic methodology features good functional group tolerance and avoids metal salts as the external oxidants. The proposed mechanism suggests that the reaction proceeds through arene C-H activation, allene insertion, and C-N coupling.
Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes
Too, Pei Chui,Wang, Yi-Feng,Chiba, Shunsuke
, p. 5688 - 5691 (2011/03/23)
A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl 2]2 - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N - O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.
New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines
Alonso, Rafael,Campos, Pedro J.,Garcia, Barbara,Rodriguez, Miguel A.
, p. 3521 - 3523 (2007/10/03)
An efficient photochemical approach for the unusual generation of six-membered heterocyclic rings is reported. Iminyl radicals, generated by the irradiation of acyloximes, participate in intramolecular cyclization processes and in intermolecular addition-intramolecular cyclization sequences.
