108694-41-3Relevant academic research and scientific papers
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.
Copper-catalyzed synthesis of N-aryl acridones from 2-amino benzophenones and aryl boronic acids via sequential double oxidative C–N coupling
He, Yang,Xu, Liang,Zhang, Jinli,Wei, Yu
, (2019/12/27)
Pot-economic synthesis of N-aryl acridones was performed with 2-aminobenzophenones and aryl boronic acids as starting materials. Cu-catalyzed chelation-assisted oxidative C–N cross-coupling reactions were well merged with the following intra-molecular oxidative dehydrogenative C–H amination reactions under an air atmosphere. The use of reagent capsules can further resolve the compatibility problem of reagents and simplify the operational process, providing a more straightforward access to the target products.
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.
Synthesis of N-arylindazoles and benzimidazoles from a common intermediate
Wray, Brenda C.,Stambuli, James P.
supporting information; experimental part, p. 4576 - 4579 (2010/11/20)
A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields. The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles. This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals.
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)
