6092-74-6

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 501-53-1 benzyl chloroformate 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 1483-73-4 diphenyliodonium bromide 
• 84447-15-4 phenylhydroxylamine oxalate 
• 98-95-3 nitrobenzene 
• 1157855-07-6 benzyl N-phenyl-N-(benzoxycarbonyloxy)carbamate 

Downstream Products

• 76570-51-9 N-benzyloxycarbonyl-N-phenyl-O-methylhydroxylamine 
• 65440-92-8 (2-Benzyloxycarbonylaminophenyl)oxalessigsaeuredimethylester 
• 1105707-48-9 N-tert-butoxy-N-Cbz-benzenamine 
• 91075-20-6 2-Benzenesulfonylmethyl-indole-1-carboxylic acid benzyl ester 
• 371-40-4 4-fluoroaniline 
• 214610-12-5 benzyl 2-oxoindoline-1-carboxylate 
• 1258876-09-3 C₁₈H₁₉NO₄ 
• 1218786-36-7 N-Cbz-2-(2',2',2'-trichloroacetylamino)-aniline 
• 1161512-86-2 C₁₉H₂₁NO₃ 

Relevant academic research and scientific papers

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

Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

The use of readily available hydroxamic acids as reagents for the chemoselective (ortho-amino)arylation of amides is described. This reaction proceeds under metal-free, mild conditions, displays a very broad scope, and constitutes a direct approach for the metal-free attachment of aniline residues to carbonyl derivatives.

Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates

An efficient one-pot procedure for the zinc-mediated reduction of nitroarenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixt

Enantioselective synthesis of 2-isoxazolines by a One-flask conjugate addition/oxime-transfer process

A study was conducted to demonstrate a new catalytic enantioselective method to prepare 5-substituted 2-isoxazolines that applied a small organic catalyst as the source of chirality and enabled the use of different α-β-unsaturated aldehydes as starting materials. The aldehyde and acetone oxime were added to a solution of amine and benzoic acid in toluene at 0 °C. A precooled solution of H2SO4 in MeOH was added and the resulting solution was stirred for 15 minutes at 0 °C after stirring the reaction mixture at 0 °C for the indicated period of time. A saturated aqueous solution of NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic extracts were dried and concentrated, while the residue was purified by flash chromatography to afford the products. The results show that the presence of a strong acid in the reaction mixture induced the formation of similar catalytic species in the reactions.

Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement

Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization

Studies on the Preparation of N-Alkyl-O-phenylhydroxylamines

Several possible routes to the title compounds have been investigated.The reaction of N-hydroxycarbamates (1) with diphenyliodonium bromide gave, unexpectedly, N-hydroxy-N-phenylcarbamates (2), while N-methyl-N-hydroxycarbamates (6) gave 2-(N-methyl-N-alkoxycarbonylamino)phenols (7).Mechanistic aspects of the N-arylations and subsequent rearrangements are discussed.The desired N-alkyl-O-phenylhydroxylamines were obtained by the reduction of O-phenyloximes (15) with sodium cyanoborohydride.