27451-20-3

Usage

InChI:InChI=1/C11H13NO3/c1-8-4-6-11(7-5-8)12(9(2)13)15-10(3)14/h4-7H,1-3H3

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 108-24-7 acetic anhydride 
• 1403889-59-7 S-2-(acetoxy(p-tolyl)amino)-2-oxoethyl O-ethyl carbonodithioate 
• 1403889-53-1 N-acetoxy-N-(4-methylphenyl)-2-chloroacetamide 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 1403889-48-4 N-(4-methylphenyl)-2-chloro-N-hydroxyacetamide 

Downstream Products

• 36804-51-0 1-(5-methyl-2,3-diphenyl-1H-indol-1-yl)ethan-1-one 
• 27451-21-4 N-hydroxy-N-(p-tolyl)acetamide 

Relevant academic research and scientific papers

Rhodium-Catalyzed Annulation of N-Acetoxyacetanilide with Substituted Alkynes: Conversion of Nitroarenes to Substituted Indoles

A general and efficient rhodium-catalyzed redox-neutral annulation of N-acetoxyacetanilides, readily accessible from nitroarenes, with alkynes has been accomplished for the synthesis of substituted indole derivatives. A wide range of substituted 2,3-diarylindoles were achieved from various substituted N-acetoxyacetanilides and symmetrical/unsymmetrical alkynes in good to excellent yields. The developed method was successfully integrated with the synthesis of N-acetoxyacetanilides for the efficient one-pot synthesis of indoles from nitroarenes. The important features are the introduction of N-acetoxyacetamide as a new directing group, redox-neutral annulation, an additive-free approach, wide functional group tolerance, an intramolecular version, and a one-pot reaction of nitroarenes. The method was further extended to the synthesis of potent higher analogues of indole, viz., pyrrolo[3,2-f]indoles and dibenzo[a,c]carbazoles. In addition, a plausible mechanism was proposed based on the isolation and stoichiometric study of a potential aryl-Rh intermediate.

An unusual synthesis of N-unsubstituted benzazepinones

A short route to novel bicyclic N-unprotected benzazepinones is described starting from N-acetoxyanilides involving radical addition and cyclization with concomitant homolytic rupture of the N-O bond.

Indium mediated reductive acylations of nitroarenes towards N,O-diacylated N-arylhydroxylamines

By applying indium, Ac2O, MeOH, and catalytic amount of InCl3 in CHCl3 solution, nitroarenes were transformed into N,O-diacylated N-arylhydroxylamines in moderate to excellent yields.

A novel one pot reductive acetylation of nitroarenes

Nitroarenes are reductively acetylated in one pot to the corres, ponding N-arylacetamides and N-(acetyloxy)-N-arylacetamides with Zn and Ac2O in presence of acidic Al2O3 in dichloromethane at room temperature.

Synthesis of N,O-Diacetylated N-Arylhydroxylamines by Reduction of Nitroaromatics with Zinc and Acetic Anhydride

Reduction of nitroaromatic compounds with zinc and acetic anhydride in dichloromethane gave N,O-diacetylated N-arylhydroxylamines in good yields under mild conditions.