119464-88-9

Upstream product

• 106-43-4 para-chlorotoluene 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 106-38-7 para-bromotoluene 
• 98-80-6 phenylboronic acid 
• 1021234-05-8 2-(p-tolylamino)benzonitrile 
• 5720-05-8 4-methylphenylboronic acid 
• 17852-28-7 2-amino-5-methylbenzophenone 
• 589-92-4 1-methylcyclohexan-4-one 
• 108-94-1 cyclohexanone 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 

Downstream Products

• 24725-28-8 9-phenyl-acridine-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions

An efficient and practical method for the synthesis of medicinally important acridines from readily available o-aminoaryl ketones and arylboronic acids was developed using copper(II)-mediated relay reactions that involve intermolecular Chan-Lam cross-coupling and subsequent intramolecular Friedel-Crafts-type reactions. A sole promoter, i.e., Cu(OTf)2, was used; therefore, strongly acidic and basic conditions, nonreadily available or expensive substrates, additives, and noble-metal catalysts were not needed.

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

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.

Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water

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.

Synthesis of Substituted Acridines through a Palladium-Catalyzed Condensation/Cyclization/Tautomerization Sequence

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.

Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant

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.).

Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives

A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.