2887-98-1

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 4897, 1988 DOI: 10.1021/jo00256a001

InChI:InChI=1/C10H11NO/c1-9(11-12)7-8-10-5-3-2-4-6-10/h2-8,12H,1H3/b8-7+,11-9+

Upstream product

• 122-57-6 1-Phenylbut-1-en-3-one 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 22921-89-7 1-(4-phenylbut-3-en-2-ylidene)-2-phenylhydrazone 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 104-55-2 3-phenyl-propenal 
• 96-29-7 ethyl methyl ketone oxime 
• 100-52-7 benzaldehyde 

Downstream Products

• 1722-73-2 (2E,3E)-4-phenylbut-3-en-2-one O-acetyl oxime 
• 13180-93-3 2-[(Z)-1-Methyl-3-phenyl-prop-2-en-(E)-ylideneaminooxy]-3,5-dinitro-benzoic acid methyl ester 
• 70265-91-7 3-methyl-5-phenyl-4,5-dihydro-isoxazol-4-ol 
• 17953-17-2 3.3-Dinitro-1-phenyl-buten-⁽¹⁾ 
• 17953-18-3 2.3.3-Trinitro-1-phenyl-buten-⁽¹⁾ 
• 1008-75-9 3-methyl-5-phenylisoxazole 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 136229-96-4 3-methyl-2-oxy-5-phenyl-pyrazol-1-ol 
• 119-65-3 isoquinoline 
• 91-63-4 2-methylquinoline 
• 2550-26-7 4-Phenyl-2-butanone 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 61247-78-7 (E)-N-(4-phenylbut-3-en-2-yl)benzamide 
• 138963-86-7 N-(1-phenylbutan-3-yl)benzamide 

Relevant academic research and scientific papers

Catalytic Nitrosation of Styrene by Nitric Oxide in the Presence of Cobalt Complex and BH4-

Co(DMGH)2(py)Cl (DMGH = mono anion of dimethylglyoxime, py = pyridine) catalyses the regioselective hydronitrosation of styrene to yield acetophenone oxime.

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones

A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts

The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.

Synthesis of oximes from the corresponding of organic carbonyl compounds with NH2 OH.HCl and oxalic acid

The oximation of a variety of aldehydes and ketones was carried out with NH2 OH?HCl in the presence of oxalic acid as catalyst under reflux conditions. The reactions were performed in CH3 CN with excellent yields(90-95%) of products in appropriate times (55-90 min).

O-iodoxy benzoic acid–mediated synthesis of 3,5-diarylisoxazoles and isoxazole-3-carboxylic acids

A new, convenient, ecofriendly synthesis of 3,5-diarylisoxazoles is reported from a,b-unsaturated ketoximes. Similarly, a novel synthesis of isoxazole carboxylic acids is also reported. Both the methods use efficient, environmentally friendly, and nontoxic iodoxybenzoic acid (IBX) as an oxidative cyclizing reagent. Easy procedure, environmentally benign reaction conditions, and nontoxicity are advantages to the methodology.

Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed.

A convenient one-pot method of converting alcohols into oximes

The one-pot conversion of primary and secondary alcohols into oximes is reported using chromium trioxide supported on alumina and hydroxylamine hydrochloride under solvent free condition. This oxidation-oxime formation reaction has been applied to a range of aliphatic and benzylic alcohols.