1352136-18-5Relevant academic research and scientific papers
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.
A magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle: An efficient and recyclable solid molecular catalyst for Suzuki-Miyaura cross-coupling of 9-chloroacridine
Deng, Qinyue,Shen, Yajing,Zhu, Haibo,Tu, Tao
supporting information, p. 13063 - 13066 (2017/12/15)
A robust magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle has been readily synthesized by directly anchoring the structural defined acenaphthoimidazolylidene palladacycle with a long tail on magnetic nanoparticles (MNPs), and functioned as a solid molecular catalyst and exhibited extremely high catalytic activity towards the challenging Suzuki-Miyaura cross-coupling reactions between less-studied heterocyclic 9-chloroacridine and diverse boronic acids. Remarkably, the catalyst could be used 5 times without obvious loss of activity highlighting the efficiency of our strategy of immobilization of previledged catalysts.
Regioselective C-H bond functionalizations of acridines using organozinc reagents
Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
supporting information; experimental part, p. 308 - 310 (2012/01/05)
Despite the recent advance in C-H bond functionalization chemistry, the C-H bonds in the acridine ring system, which is an important scaffold in medicinal and material science, have met with limited success, due, in part, to the lack of activated C-H bonds adjacent to the ring nitrogen atom. Herein, several protocols that can effect the regioselective arylation and alkylation of acridines at the C-4 and C-9 positions are described.
