71825-04-2

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 136696-42-9 2-acetyl-3,4-dimethylthiazolium triflate 
• 62-53-3 aniline 
• 616-38-6 carbonic acid dimethyl ester 
• 586-96-9 Nitrosobenzene 
• 61495-67-8 2-Acetyl-1,3-dimethylbenzimidazolium iodide 
• 631-57-2 Acetyl cyanide 
• 136696-46-3 Trifluoro-methanesulfonate2-[1-hydroxy-1-(N-phenyl-aminooxy)-ethyl]-3,4-dimethyl-thiazol-3-ium; 

Downstream Products

• 19958-58-8 N-benzoyl-N-phenyl-O-(acetyl)hydroxylamine 
• 19958-60-2 O-acetyl-N-(4-nitrobenzoyl)-N-phenylhydroxylamine 
• 119878-68-1 8-phenylamino-2′-deoxyguanosine 
• 37682-91-0 N-methyl-N,N′-diphenylhydrazine 
• 39837-50-8 N,N-diethyl-N'-phenyl-hydrazine 
• 495-48-7 azoxybenzene 

Relevant academic research and scientific papers

Identification of New DNA Adducts of Phenylnitrenium

Phenylnitrenium ion (PhNH+) may bind to nucleophiles through nitrogen as well as through C2 or C4 carbons. However, only adducts of the former type have been hitherto reported after its reaction with purine nucleosides. In this study, reactions of N-acetoxyaniline (PhNHOAc), a precursor to PhNH+, with 2′-deoxyadenosine (dA), 2′-deoxyguanosine (dG), and with DNA in vitro at physiological conditions are described. The reaction of PhNHOAc with dA followed by a hydrolytic deribosylation afforded 8-phenylaminoadenine (C8-PhNHA) together with a smaller amount of N6-(4-aminophenyl)adenine (N6-4APA). A similar reaction with dG afforded 8-phenylaminoguanine (C8-PhNHG) together with traces of 7-(4-aminophenyl)guanine (N7-4APG). The same adducts were found also in the DNA treated with PhNHOAc, and all of them were identified by comparison of their HPLC retention times and MS2 spectra with a set of synthesized authentic adenine adducts at C2, C8, N7, and N6 positions and guanine adducts at C8, N7, and N2 positions. The newly identified minor adduct, N7-4APG, represents the first proof of arylnitrenium adduction at the N7 position of dG, which is the prominent site of attack by most C-electrophiles.

A nanostarch functionalized ionic liquid containing imidazolium cation and cobalt chelate anion for the synthesis of carbamates from amines and dimethyl carbonate

A new nanostarch functionalized ionic liquid containing imidazolium cation and cobalt chelate anion was synthesized and tested for the one pot synthesis of carbamates by the reaction of amines and dimethyl carbonate (DMC), affording excellent yield of the products under solvent free mild reaction conditions. The synthesized ionic liquid was easily recovered and reused several times without any loss in catalytic efficiency.

Reactions of 2-acylthiazolium salts with N-arylhydroxylamines

2-Acylthiazolium salts, easily obtained by alkylation of the corresponding 2-acylthiazoles with methyl triflate, react with N- arylhydroxylamines to furnish the O-acyl derivatives of relevance in the induction of cancer by aromatic mines.

Reduction of Nitrosobenzene by 2-(α-Hydroxyethyl)-3,4-dimethylthiazolium Salts

Nitrosobenzene in a basic medium is reduced by 2-(α-hydroxyethyl)- or 2-(α-hydroxybenzyl)-3,4-dimethylthiazolium trifluoromethanesulfonate to yield the intermediate hydroxylamine and 2-acyl-3,4-dimethylthiazolium trifluoromethanesulfonate, with acylation of the former by the latter giving the final products.

Selective O-acylation of aromatic hydroxylamines by 2-acylimidazolium and 2-acylbenzimidazolium salts

2-Acyl 1,3-dimethylbenzimidazolium and 2-acyl 1,3-dimethylimidazolium salts react with N-aromatic hydroxylamines in the presence of base to give the O-acyl derivatives.

2-Acyl Thiazolium Salts as Selective Agents for the O-Acylation of Aromatic Hydroxylamines

2-Acyl-3,4-dimethylthiazolium triflates, modelled upon the biologically important 2-acyl thiamine derivatives, react in neutral media specifically with the oxygen atom of N-aryl hydroxylamines to give rise to tetrahedral intermediates, which collapse to t

N-Aryl-O-(α-aminoacyl)hydroxylamines: Model Reactions with Deoxyguanosine, Guanosine and 5'-Guanosinemonophosphate for the Activation of Monocyclic Aromatic Amines (e.g. Phenacetin) into Ultimate Carcinogens

In in vitro model reactions of the activation of monocyclic aromatic amines by α-amino acids it is shown that α-aminohydroxamic acids 8 and 9 rearrange base-catalyzed to N-(α-aminoacyloxy)arylamines 10 and 11 which react with bionucleophiles such as deoxyguanosine (dG) (12), guanosine (G) (13) and 5'-guanosinemonophosphate (5'-GMP) (14) to form adducts.We describe the regioselective formation of the C-8 adducts of 4-chloroaniline (15), aniline (16), 4-methylaniline (17), and 4-methoxyaniline (18), respectively, , and also of N-(guanosine-8-yl)-4-methylaniline (21) and 8-(4-methylanilino)-5'-guanosinemonophosphate (22).Similar reactions of the N-(acetoxy)arylamines 20, which are very likely to be "ultimate" carcinogens of aromatic amines, lead to the same C-8 adducts 15-18, 21, and 22 in comparable yields.These in vitro reactions thus show that the N-(α-aminoacyloxy)arylamines 10 and 11 react like the N-(acetoxy)anilines 20 as "ultimate" carcinogens.Therefore, the activation of aromatic hydroxylamines by O-α-aminoacylation is of similar quality as by O-acetylation.