A- -arylamines

Keywords aryl halide, secondary amine, /V-alkylation, microwave irradiation, A-arylamine... 

W. P. Jencks, M. Gresser, M. S. Valenzuela, and F. C. Huneeus. Acetyl coenzyme a arylamine acetyltransferase. Measurement of the steady state concentration of the acetyl-enzyme intermediate. J. Biol. Chem., 247 3756-3760, 1972. 

A new method of synthesis of A-alkylphthalimides (79) via alkylation of phthalim-ide in dry media under microwave irradiation was carried out by Bodgal et al. (1996). The reactions were performed by simply mixing phthalimide with an alkyl halide adsorbed on potassium carbonate to give a good yield of the product. Yadav and Subba Reddy (2000) reported a novel and efficient synthesis of A-arylamines (80) by the reaction of activated aryl halides with secondary amines in the presence of... 

The N-acetylation of different aryl- and arylalkylamines, using acetyl-CoA as the acetyl donor, proceeds when catalyzed by acetyl-Co A arylamine N-acetyltransferase. A natural substrate is serotonin, which is converted to N-acetylserotonin in the pineal gland and other regions of the brain. 

NaNHR, or NaNR2. Lithium dialkylamides also react with aryl halides to give the A-arylamine. With these reagents, the benzyne mechanism generally operates, so cine substitution is often found. The reaction of an amine, an aryl halide, and potassium tert-butoxide generates the A -aryl amine. A -Arylation was accomplished with butyllithium and a secondary amine using Ni/C-diphenylpho-sphinoferrocene (dppf). Ring closure has been effected by this type of reaction, as in the conversion of 16 to the tetrahydroquinoline. 

Nickel catalysts have been used in the reaction of aryl halides with A-alkyl aniline derivatives. Nickel catalyst also allow the conversion of aryl halides to A-arylamines via reaction with aliphatic amines. An intramolecular reaction of a... 

Summerscales JE, Josephy PD. Human acetyl Co A arylamine N-acetyltransferase variants generated by random mutagenesis. Mol Pharmacol 2004 65 ... 

Sim E, Lack N, Wang C-J, Long H, Westwood I, Fullam E, Kawamura A. Arylamine A-acetyltransferases Structural and functional implications of pol5morphisms. Toxicology 2008 254 170-183. 

In 2015, Xiao and co-workers reported an iridium complex (14)-catalyzed N-alkylation of amines with alcohols under mild conditions (100 °C) (Scheme 22) [113]. Anilines, heteroarylamines, A -alkyl-A(-arylamines, and sulfonamides could serve as A-nucleophiles. The same method can also be applied to amine-based N-... 

We reported [82] the W-arylation of imidazoles and amines with arylboronic acids with copper-exchanged fluorapatite (Cu-FAP) in methanol at room temperature. The products W-arylimidazoles and W-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the corresponding W-arylimidazoles and A-arylamines, demonstrating the versatility of the reaction. 

The regio- and enantio-selective rhodium-catalysed 5isf2 reactions between substituted anilines and racemic tertiary allylic trichloroacetimidates give a,a-disubstituted allylic A -arylamines in moderate to high (51-92%) yields with S 2 S 2 ratios from 5 1 to >99 1 and 52 to 96% ee The catalyst was prepared from [RhCl(ethylene)2]2 and trans-2,5-(4-fluorophenyl)bicyclo [2,2,2] octadiene. 

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