613-47-8

Usage

InChI:InChI=1/C10H9NO/c12-11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11-12H

Upstream product

• 581-89-5 2-nitronaphthalene 

Downstream Products

• 18271-22-2 N-(naphthalen-2-yl)benzamide 
• 106184-48-9 N-(1-bromonaphthalen-2-yl)benzamide 
• 31928-56-0 N-2-naphthyl-C-phenylnitrone 
• 122078-04-0 N¹-Methyl-N¹-phenyl-naphthalene-1,2-diamine 
• 122078-05-1 1-(2-Methylamino-phenyl)-naphthalen-2-ylamine 
• 122078-03-9 N-Methyl-N'-naphthalen-2-yl-N-phenyl-hydrazine 

Relevant academic research and scientific papers

Expeditious and Efficient ortho-Selective Trifluoromethane-sulfonylation of Arylhydroxylamines

A metal- and oxidant-free, practical and efficient method for the synthesis of highly versatile and synthetically useful ortho-trifluoromethanesulfonylated anilines from arylhydroxylamines and trifluoromethanesulfinic chloride was developed. This rapid tr

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Direct Construction of NOBINs via Domino Arylation and Sigmatropic Rearrangement Reactions

Privileged 2-amino-2’-hydroxy-1,1’-binaphthyl (NOBIN) frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal-free fashion. This protocol bears broad substrate generality and proceeds under mild reaction conditions, affording diversified NOBINs in high efficiency with absolute regiocontrol during the rearrangement process. Optically active product was accessible by chiral N-heterocyclic carbene-catalyzed kinetic resolution in one pot or diastereoselective [3,3]-rearrangement guided by a removable chiral auxiliary. Remarkably, diarylchloronium and diarylbrominium salts have been employed as arylation reagents for the first time in assembling such representative biaryl frameworks.

Cascade Approach to Highly Functionalized Biaryls by a Nucleophilic Aromatic Substitution with Arylhydroxylamines

A transition-metal free synthesis of highly functionalized 2-hydroxy-2′-amino-1,1′-biaryls from N-arylhydroxylamines has been developed. This operationally simple and readily scalable approach relies on a cascade of reactions that initially generates transient N,O-diarylhydroxylamines, via direct O-arylation, which then undergo rapid [3,3]-sigmatropic rearrangement and subsequent rearomatization to form NOBIN-type products. These structurally diverse functionalized biaryls are obtained under mild conditions in good to excellent isolated yields.

The Cycloadditions of Nitrones with Fluoroallene

Cycloadditions of nitrones with fluoroallene proceed regiospecifically and with a remarkable stereochemical preference for addition syn to the fluorine substituent.The effects of solvent polarity on the rates and stereochemistry of these cycloadditions are reported and discussed.In general these effects are consistent with those reported for other nitrone cycloadditions, and the activation parameters are also similar.