1137-96-8

Usage

Uses

It is used as a pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 845, 1970 DOI: 10.1021/jo00828a076

InChI:InChI=1/C13H11NO/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H/b14-11-

Upstream product

• 100-52-7 benzaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 538-51-2 benzylidene phenylamine 
• 98-95-3 nitrobenzene 
• 773837-37-9 sodium cyanide 
• 243140-08-1 5(Z)-N-ethylidene-1-phenylmethanamine N-oxide 
• 74635-18-0 N-benzylmethylene nitrone 
• 586-96-9 Nitrosobenzene 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 758640-21-0 N-Benzylaniline 
• 100-51-6 benzyl alcohol 
• 591-50-4 iodobenzene 
• 501-65-5 diphenyl acetylene 
• 3376-40-7 N-benzyl-N-phenylhydroxylamine 

Downstream Products

• 110212-91-4 2,3-Diphenyl-1-oxa-6,10-dithia-2-aza-spiro[4.5]decane 
• 107081-91-4 2-<(phenylsulfonyl)methyl>-indole 
• 100-52-7 benzaldehyde 
• 107081-89-0 4-oxo-2-phenyl-3-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 107081-90-3 1,5-diphenyl-3-oxo-4-(phenylsulfonyl)-2,3,4,5-tetrahydropyrrole 
• 120850-59-1 3(R)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one 
• 120779-58-0 3(S)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one 
• 86661-72-5 2-Phenyl-3-azabenzobicyclo<4.4.1>undeca-1(10),4-dien-11-on 
• 78847-87-7 N-<α-(Dimethylamino)benzyl>phenylaminyl-N-oxid 
• 4264-35-1 2-acetylindole 
• 37129-23-0 ethyl 3-phenyl-1H-indole-2-carboxylate 
• 119027-87-1 4-carboxyethyl-2,3,5-triphenyl-4-isoxazoline 
• 3770-50-1 2-carbethoxyindole 

Relevant academic research and scientific papers

Selective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and -decorated platinum nanoparticles

Nitrones were synthesized in high yields directly from nitro compounds, aldehydes, and H2 using carbon-decorated platinum nanoparticles. The high selectivity for nitrone synthesis contrasts that of common supported metal catalysts and correspon

Urea-catalyzed construction of oxazinanes

Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.

Strain-Release Driven Cycloadditions for Rapid Construction of Functionalized Pyridines and Amino Alcohols

This paper describes the development of a new variant of stereoselective strain-release driven reactions (formal homo [3 + 2] dipolar cycloadditions) which utilize housane (1) to construct functionalized amino alcohols and pyridine-substituted cyclopentanes in two to three steps from simple and easily available building blocks (nitrones and pyridine N-oxides respectively).

Differences among the mechanisms of reaction of phenylhydroxylamine with various carbonyl compounds

In order to obtain a better knowledge of the special behavior of phenylhydroxylamine as a nucleophile, the mechanism of its reaction with 2,6-dichlorobenzaldehyde, norcamphor, and cyclohexanone, and also the hydrophobic effect on its reaction with 2,6-dichlorobenzaldehyde and benzaldehyde, was studied. The results led us to assume that the planar molecule of phenylhydroxylamine should be placed parallel to the planar molecule of benzaldehyde in order to permit the attack of the lone electron pair of the nitrogen on the carbonyl group, forming, together with a hydrogen bond between the hydroxyl group and the carbonylic oxygen atom, a packed preassociation complex. This mechanism is not observed in the case of norcamphor or 2,6-dichlorobenzaldehyde due to the steric hindrances produced by the lack of planarity of these molecules.

Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones

[Figure not available: see fulltext.] The 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to 7-arylmethylidene-6,7-dihydroindolizin-8(5H)-ones afforded novel 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones in moderate yield

High diastereoselectivity induced by intermolecular hydrogen bonding in [3?+?2] cycloaddition reaction: experimental and computational mechanistic approaches

A diastereoselective [3?+?2] cycloaddition of N-aryl substituted maleimides with N,α-diphenyl nitrone possessing 11-hydroxyundecyloxy as a flexible substituent was performed. Experimental and comprehensive mechanistic density functional theory studies reveals that intermolecular H-bonding and steric repulsive interaction predominate exo-Z and exo-E cycloaddition transition states, respectively. The reaction proceeded smoothly depending on the reactants and gave a good yield of (syn) cis-isoxazolidine or (anti) trans-isoxazolidine as a single diastereomer.

Facile approach to alkaloid-like 6/6/5/5-tetracyclic spiroheterocycles via 1,3-dipolar cycloaddition reaction of fused 1H-pyrrole-2,3-diones with nitrones

A facile synthetic approach towards 6/6/5/5-tetracyclic spiroheterocycles has been developed from the highly diastereoselective 1,3-dipolar cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with nitrones. The described novel heterocyclic systems are heteroanalogs of cytotoxic alkaloids, kibalaurifoline and gitingensine. The developed reaction represents the first example of involvement of 1H-pyrrole-2,3-diones fused at [e]-side in a 1,3-dipolar cycloaddition reaction.

Aerobic oxidation of hydroxylamines with nanoporous gold catalyst as an efficient synthetic method of nitrones Dedicated to Professor Jiro Tsuji on the occasion of his receipt of the 2014 Tetrahedron Prize

Abstract A facile preparation of nitrones has been achieved by use of unsupported nanoporous gold (AuNPore) as a heterogeneous catalyst through aerobic oxidation of N,N-disubstituted hydroxylamines with molecular oxygen as an oxidizing agent under mild conditions. A variety of amines were oxidized to the corresponding nitrones in high chemical yields. The catalyst is robust enough to be reused without leaching.

Selective oxidation of N-alkyl imines to oxaziridines using UHP/maleic anhydride system

Several structurally differentiated N-alkyl imines were oxidized to their corresponding oxaziridines using UHP/maleic anhydride system. Oxidation reaction was performed under mild conditions and oxaziridines were obtained in good to excellent yields.

Method for converting terminal alkyne into carboxylic acid and application of method in construction of gene coding library

The invention provides a method for converting terminal alkyne into carboxylic acid in construction of a gene coding compound library. The method has the advantages of good universality, mild conditions, convenient operation and high yield, and is suitable for synthesis of the gene coding compound library by a porous plate. According to the method for converting terminal alkyne into carboxylic acid in construction of the gene coding compound library, the reaction types which can be successfully applied in the gene coding library technology are increased, and the synthesis method of the gene coding compound library is simplified.