108694-41-3Relevant articles and documents
Copper-Catalyzed Electrophilic Amination of Arylboronic Acids with Anthranils: An Access to N-Aryl-2-aminophenones
Gao, Yang,Yang, Simin,Li, Yibiao,Huo, Yanping,Huang, Zongyi,Chen, Zumin,Hu, Xiao-Qiang
, p. 10222 - 10231 (2020/09/03)
An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, and operational simplicity. Moreover, a tandem C-H borylation and C-N coupling protocol has also been developed to transform simple arenes to the valuable N-aryl-2-aminophenones in one pot. Additionally, the synthetic potential of this methodology is further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
Li, Jie,Tan, Eric,Keller, Niklas,Chen, Yi-Hung,Zehetmaier, Peter M.,Jakowetz, Andreas C.,Bein, Thomas,Knochel, Paul
supporting information, p. 98 - 103 (2019/01/08)
The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap.
Nickel-Catalyzed Transformations of 2,1-Benzisoxazoles with Organozinc Reagents
Baum, Jonathan S.,Condon, Michael E.,Shook, David A.
, p. 2983 - 2988 (2007/10/02)
A novel transformation of 2,1-benzisoxazoles (anthranils) involving nitrogen-oxygen bond rupture with concomitant nitrogen-carbon bond formation by reaction with aryl-, methyl, or 2-thienylzinc chlorides in the presence of nickel catalyst is described.The products of the reaction are o-(substituted-amino)benzaldehydes and benzophenones, precursors of a series of heterocyclic derivatives, including acridines, quinolones, and the novel 7-chloro-1,3-dihydro-1,5-diphenyl-2H-1,4-benzodiazepin-2-one (21)