95888-31-6Relevant articles and documents
Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water
Ye, Xuanzeng,Xu, Beihang,Sun, Jiani,Dai, Ling,Shao, Yinlin,Zhang, Yetong,Chen, Jiuxi
, p. 13004 - 13014 (2020/11/23)
A novel palladium-catalyzed protocol for the synthesis of 9-arylacridines via tandem reaction of 2-(arylamino)benzonitrile with arylboronic acids in water has been developed with good functional group tolerance. The present synthetic route could be readily scaled up to gram quantity without difficulty. This methodology was further extended to the synthesis of a 4′-OH derivative, which showed estrogenic biological activity. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular Friedel-Crafts acylation and dehydration to acridines.
Tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C-N Coupling: Synthesis of Acridines at Room Temperature
Cao, Zifeng,Zhu, Yuan,Li, Xiaoman,He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu
, p. 10167 - 10174 (2020/09/03)
Herein, a facile intramolecular cyclization of 2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan-Evans-Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted acridines from readily available 2-amino phenyl ketones and aryl boronic acids at room temperature.
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
, 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.
Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant
Mu, Wan-Lu,Wang, Meirong,Li, Hui-Jing,Huang, Deng-Ming,Zhang, Yi-Yun,Li, Chao-Yi,Liu, Ying,Wu, Yan-Chao
supporting information, p. 4250 - 4257 (2017/12/15)
A facile oxidative annulation of cyclohexanones and 2-aminophenyl ketones that uses molecular oxygen as the sole oxidant is described. The reaction provides a direct approach to acridines, a structural motif for a large number of fluorescent sensors, functional materials, ligands, and pharmaceuticals. In the presence of a palladium catalyst, high regioselectivity is observed when using non-symmetric 3-substituted cyclohexanones. With the use of oxygen as the terminal redox moderator, the electron gap of the global redox condensation process is filled and the reaction efficiency is significantly promoted. This protocol possesses many advantages such as using non-hazardous oxidant and readily available starting materials, high regioselectivity, and water as the only by-product. (Figure presented.).
Synthesis of Substituted Acridines through a Palladium-Catalyzed Condensation/Cyclization/Tautomerization Sequence
Chen, Xiangui,Xie, Yanjun,Li, Cheng,Xiao, Fuhong,Deng, Guo-Jun
supporting information, p. 577 - 581 (2017/02/05)
Herein, we report an efficient strategy for the synthesis of 9-aryl-substituted acridines from cyclohexanones and 2-aminobenzophenones in the presence of a palladium catalyst. Molecular oxygen is applied as a green oxidant. Various cyclohexanones acted as the aryl source to construct the nitrogen-containing heterocycles through a condensation/cyclization/tautomerization sequence.
The Reaction of Benzyne with Imines
Fishwick, Colin W. G.,Gupta, Ramesh C.,Storr, Richard C.
, p. 2827 - 2829 (2007/10/02)
The isolation of acridines from reaction of benzyne with the imines, N-benzylideneaniline and N-benzylidene-4-chloroaniline, and the amidines, N,N-dimethyl-N'-phenylformamidine and N-phenyliminomethylpyrrolidine, provides unambiguous evidence for the formation of transient benzazetidines by 2 + 2 cycloaddition.
