117296-15-8

Upstream product

• 169170-03-0 N-methyl-N-phenylanthranilic acid methyl ester 
• 73323-82-7 2-(N-Methyl-N-phenylamino)-benzoic acid 
• 100-61-8 N-methylaniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 62-53-3 aniline 
• 91-40-7 2-(phenylamino)benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 208664-53-3 2-((N-methyl-N-phenyl)amino)benzaldehyde 
• 260-94-6 acridine 
• 602-56-2 9-phenylacridine 
• 82772-34-7 [2-(methylanilino)phenyl](phenyl)methanole 
• 1859-76-3 2-(methylamino)benzophenone 
• 209412-50-0 2-(Methyl-phenyl-amino)-benzaldehyde oxime 
• 209412-43-1 [2-(methylanilino)phenyl](phenyl)methanone 
• 209412-61-3 [1-[2-(Methyl-phenyl-amino)-phenyl]-meth-(E)-ylideneaminooxy]-acetic acid 
• 209412-73-7 [1-[2-(Methyl-phenyl-amino)-phenyl]-meth-(E)-ylideneaminooxy]-ethaneperoxoic acid tert-butyl ester 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 30713-65-6 9-hydroxy-9,10-dihydro-10-methylacridine 

Relevant academic research and scientific papers

Substrate-Controlled Selectivity Switch in the Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and CO2

The transition-metal-free multicomponent coupling involving arynes, aromatic tertiary amines, and CO2 is reported. The reaction exhibits switchable selectivity depending on the electronic nature of the aromatic amines used. With amines bearing electron-releasing/neutral groups as the nucleophilic trigger, the reaction afforded 2-arylamino benzoates via a nitrogen to oxygen alkyl group migration. Employing electron-deficient amines in the reaction furnished 2-aminoaryl benzoates proceeding via the aryl to aryl amino group migration resembling a Smiles rearrangement.

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones

A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates

Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.

Pyridyl-substituted imidazoles, compositions containing same and methods of use thereof

Novel imidazole of the formula: STR1 wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R1 and R2 are hydrogen atom or are combined together to form a group of the formula: --(CH2)q --; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as anti-ulcer agents.