1795-83-1

Upstream product

• 32954-65-7 N,O-diacetylphenylhydroxylamine 
• 35225-46-8 N,N'-dihydroxy-N,N'-diphenyl-methanediyldiamine 
• 108-24-7 acetic anhydride 
• 100-65-2 N-Phenylhydroxylamine 
• 507-09-5 thioacetic acid 
• 10557-63-8 N-phenyl-N-trimethylsilylacetamide 
• 3451-88-5 1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine 
• 586-96-9 Nitrosobenzene 
• 35301-62-3 N-phenyl-N-acetyl-O-methylhydroxylamine 
• 75-07-0 acetaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 631-57-2 Acetyl cyanide 
• 75-36-5 acetyl chloride 
• 98-95-3 nitrobenzene 

Downstream Products

• 91631-52-6 N-sulfonoxyacetanilide pyridinium salt 
• 576-15-8 N-acetylindole 
• 586-96-9 Nitrosobenzene 
• 1118-69-0 N-isopropylacetamide 
• 88342-83-0 dimethyl 1-acetyl-2-hydroxy-2,3-dihydroindole-2,3-dicarboxylate 
• 37682-91-0 N-methyl-N,N′-diphenylhydrazine 
• 588-46-5 N-(phenylmethyl)acetamide 
• 101218-45-5 methyl 3,4-di-O-acetyl-1,2-O-<1-(N-phenylaminooxy)ethylidene>-α-D-glucopyranuronate 
• 13214-41-0 methyl (acetanailide-N-yl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 98911-14-9 N-phenylacetohydroxamic acid 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 98911-10-5 3,4,6-tri-O-acetyl-1,2-O-<1-(N-acetylanilino-oxy)ethylidene>-α-D-glucopyranose 
• 134810-86-9 N-Phenyl-N-propionyloxy-acetamide 
• 27125-80-0 O-benzoyl-N-phenyl-acetohydroxamic acid 
• 27688-17-1 N-Phenyl-N-[2-(2,4,5-trichloro-phenoxy)-acetoxy]-acetamide 

Relevant academic research and scientific papers

The Solvolysis of N-Acetoxy-2-acetylaminofluorene and N-Acetoxy-4-acetylaminobiphenyl: Delicate Balance between Nitrenium Ion Formation and Hydrolysis

The solvolysis of N-acetoxy-2-acetylaminofluorene in aqueous acetone at neutral pH proceeds exclusively with nitrenium ion formation while under the same conditions, the 4-aminobiphenyl analogue undergoes exclusive acyl-oxygen scission.

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.

Enzymatic and mechanistic studies on the formation of N- phenylglycolohydroxamic acid from nitrosobenzene and pyruvate in spinach leaf homogenate

The biotransformation mechanism of an unknown metabolite formed enzymatically from nitrosobenzene (NOB) and pyruvate in spinach (Spinacea oleracea L.) was investigated using spinach leaf homogenate. The unknown metabolite was identified as N-phenylglycolo

Transketolase Catalyzed Synthesis of N-Aryl Hydroxamic Acids

Hydroxamic acids are metal-chelating compounds that show important biological activity including anti-tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non-natur

Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Synthesis method of N-acylhydroxylamine

The invention relates to a synthesis method of N-acylhydroxylamine, which comprises the following steps: starting from o-diketone and a nitroso compound, and adding an acid thereby efficiently obtaining the structure of N-acylhydroxylamine under the irradiation of visible light or ultraviolet light, wherein a part of the obtained product is an important biomedical chemical intermediate. Accordingto the method, the o-diketone and the nitroso compound which are cheap and easy to obtain are used as raw materials, only visible light or ultraviolet light irradiation is needed, cheap acid is addedin the reaction process, a catalyst or a metal compound is not needed, and only water can be used as a solvent in mass production. The whole production process is environmentally friendly, economical,efficient and low in cost, and has very remarkable advantages compared with the conventional production process.

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

TRIFLUOROMETHOXYLATION OF ARENES VIA INTRAMOLECULAR TRIFLUOROMETHOXY GROUP MIGRATION

The present invention provides a process of producing a trifluoromethoxylated aryl or trifluoromethoxylated heteroaryl having the structure: (I), wherein A is an aryl or heteroaryl, each with or without subsutitution; and R1 is -H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), - (alkylaryl), - (alkylheteroaryl), -NH-(alkyl), -N(alkyl)2, -NH-(alkenyl), -NH-(alkynyl) -NH-(aryl), -NH-(heteroaryl), -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), -S-(alkyl), -S- (alkenyl), -S-(alkynyl), -S-(aryl), or -S-(heteroaryl), comprising: (a) reacting a compound having the structure: (II), with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: (III); and (b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: (I).

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.