126901-23-3

Upstream product

• 66682-84-6 N-(4-Methoxyphenyl)acetohydroxamsaeure 
• 100-61-8 N-methylaniline 
• 126875-71-6 Phenylalanin-N-(4-methylphenyl)hydroxamsaeure 
• 126901-26-6 N-(4-Methoxyphenyl)pivalohydroxamsaeure 
• 126875-78-3 (N^α-Benzylglycin)-N-(4-methoxyphenyl)hydroxamsaeure 
• 126901-22-2 (N^α-Benzylalanin)-N-(4-methoxyphenyl)hydroxamsaeure 
• 917-54-4 methyllithium 
• 21650-49-7 (E)-1-(4-methoxyphenyl)-2-phenyldiazene 
• 126901-18-6 2-Bromo-N-hydroxy-N-(4-methoxy-phenyl)-propionamide 
• 126926-32-7 2-Bromo-N-hydroxy-N-(4-methoxy-phenyl)-acetamide 
• 4546-20-7 p-methoxyphenylhydroxylamine 

Relevant academic research and scientific papers

Transitional-Metal-Activated Organic Compounds, XXXV. - ortho-Alkylation of Aromatic Azo Compounds with Alkyllithium Reagents and Lithium Trimethylferrate(1-)

Whereas methyllithium reacts with 4-(dimethylamino)-, 4-amino-, and 4-methoxyazobenzene, respectively, by ortho-methylation of the electron-rich phenyl residue of the azo compound, (CH3)3FeLi ortho-methylates the less electron-rich phenyl group of 4-(dimethylamino)azobenzene.A mechanistic rationalization is given for both reaction modes.Key Words: Lithium, organo compounds / Iron, organo compounds / Azo compounds / ortho-Alkylation

N-Aryl-O-(α-aminoacyl)hydroxylamines: Model Reactions for the Activation of Monocyclic Aromatic Amines into Ultimate Carcinogens with α-Amino Acids

The rearrangement of the new α-aminohydroxamic acids 15 and 18 to the likewise new N-(α-aminoacyloxy)arylamines 19 and 20, respectively, is observed in amine-catalyzed model reactions.N-(acyloxy)arylamines such as 19 and 20 are indicated to be ultimate carcinogens of aromatic amines which are able to react with bionucleophiles such as the DNA bases.The formation of 19 and 20 was proven by trapping these reactive intermediates with the model nucleophile N-methylaniline (21) to give the hydrazines 22 and - depending on the substituent in 19 and 20 - the so-called ortho amination products 23.Analogous reactions of the aceto- and pivalohydroxamic acids 24 and 25 lead also to the adducts 22 and 23, respectively, in comparable yields.These results demonstrate that the O-α-aminoacylation as shown here may be similarily used in model reactions for the activation of carcinogenic aromatic amines as the O-acetylation.

N-ACETOXY-4-METHOXYANILINE, A MODEL COMPOUND FOR THE ULTIMATE CARCINOGEN OF THE PHENACETIN RELATED 4-ETHOXYANILINE

We prepared and trapped in situ with N-methylaniline and deoxyguanosine (dG) the three N-acyloxy-4-methoxyanilines 7a-c.Furthermore, we synthesized N-acetoxy-4-methoxyaniline 7a and reacted it with dG.Especially 7a is a model for the ultimate carcinogen o