Synthesis Of Oximes Research Articles

ChemInform Abstract: Electrochemical Tandem Synthesis of Oximes from Alcohols Using KNO3 as the Nitrogen Source, Mediated by Tin Microspheres in Aqueous Medium.

Electrochemical oximation of alcohols was realized with KNO(3) as the nitrogen source mediated by tin microspheres.

Synthesis of Oximes with NH2OH.HCl/DOWEX(R)50WX4 System

AbstractThe oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z‐aldoximation isomers of aldehydes and E‐oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.

Selective Tandem Synthesis of Oximes from Benzylic Alcohols Catalyzed with 2, 3-Dichloro-5, 6-dicyanobenzoquinone

E-mail: gh_aghapour@du.ac.irReceived December 20, 2011, Accepted January 3, 2012In spite of many reports in the literature concerning with oxidation of benzylic alcohols to carbonyl compoundswith 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in stoichiometric amounts or even more, we surprisinglyfound that benzylic alcohols are directly oxidized to oximes using a catalytic amount of DDQ in the presenceof hydroxylamine hydrochloride under solvent-free conditions. The present tandem catalytic method can beefficiently used for preparation of oximes in the presence of some other functional groups with excellentchemoselectivity. Key Words : Alcohol, Oxime, 2,3-Dichloro-5,6-dicyanobenzoquinone, Tandem synthesisIntroductionTandem processes that involve multiple chemical trans-formations in a single-pot with minimal work up and lesswaste generation have revolutionized synthetic chemistry inrecent years.

Electrochemical tandem synthesis of oximes from alcohols using KNO3 as the nitrogen source, mediated by tin microspheres in aqueous medium

Electrochemical oximation of alcohols was realized with KNO(3) as the nitrogen source mediated by tin microspheres.

ChemInform Abstract: Efficient Microwave‐Assisted Synthesis of Oximes from Acetohydroxamic Acid and Carbonyl Compounds Using BF3·OEt2 as the Catalyst.

Abstract An efficient synthesis of oximes by reaction of carbonyls with acetohydroxamic acid using BF3·OEt2 as a catalyst is described.

A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry

BackgroundSynthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds. Nitriles, amides via Beckmann rearrangement, nitro compounds, nitrones, amines, and azaheterocycles can be synthesised from oximes. They also find applications for selective α-activation. In inorganic chemistry, oximes act as a versatile ligand.Several procedures for the preparation of oximes exist, but, most of them have not addressed the green chemistry issue. They are associated with generation of pollutants, requirement of high reaction temperature, low yields, lack of a generalized procedure, etc. Hence, there is a demand for developing an efficient, convenient, and non-polluting or less polluting alternative method for the preparation of oximes. In this context, bismuth compounds are very useful as they are cheap in general, commercially available, air stable crystalline solids, safe, and non-toxic, hence easy to handle.ResultsCarbonyl compounds (aliphatic, heterocyclic, and aromatic) were converted into the corresponding oximes in excellent yields by simply grinding the reactants at room temperature without using any solvent in the presence of Bi2O3. Most importantly, this method minimizes waste disposal problems, provides a simple yet efficient example of unconventional methodology and requires short time.ConclusionsWe have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under solvent-free grinding condition.

Microwave-promoted one-pot conversion of alcohols to oximes using 1-methylimidazolium nitrate, [Hmim][NO3], as a green promoter and medium

A wide variety of oximes were prepared from different types of alcohols with hydroxylamine hydrochloride using 1-methylimidaziloum nitrate, [Hmim][NO3], ionic liquid as a reaction medium and promoter under microwave irradiation. This protocol provides a one-pot oxime synthesis with high yields that is facile, eco-friendly and the ionic liquid can be recovered and reused.

Efficient microwave-assisted synthesis of oximes from acetohydroxamic acid and carbonyl compounds using BF 3·OEt 2 as the catalyst

An efficient synthesis of oximes by reaction of carbonyls with acetohydroxamic acid using BF 3·OEt 2 as a catalyst is described.

Total Synthesis of (+)-Epilupinine via An Intramolecular Nitrile Oxide-Alkene Cycloaddition

Total synthesis of (+)-epilupinine was accomplished in nine steps and in 48% overall yield, in which INOC was used as the key step for the construction of the quinolizidine skeleton. We found that it was an extremely difficult task to prepare the key intermediates (R)-N-(3-nitropropyl)-2-vinylpiperidine or (R)-(2-vinylpiperid-1-yl)propanal by routine methods. Thus, by using Fukuyama's oxime synthesis, a general method was developed for highly efficient conversion of 3-(N,N-dialkylamino)propanols into 3-(N,N-dialkylamino)propanal oximes without using the corresponding aldehydes.

ChemInform Abstract: A Facile Synthesis of Oximes (II) from 1-Nitro-1-alkenes (I) by Lead Reduction.

ChemInform Abstract: A Facile Synthesis of Oximes (II) from 1-Nitro-1-alkenes (I) by Lead Reduction.

ChemInform Abstract: Nitrile Oxide-BF3 Complex as Electrophilic Moiety Towards Aromatic Systems: Stereospecific Synthesis of Oximes.

Abstract Aromatic Oximes are obtained stereospecifically by action of Nitrile Oxide-BF 3 complexes on Aromatic Compounds.

Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents

Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/ O-methyloximes 1–14/15–28/29–42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/ O-methyloximes 43–48/49–54/55–60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria ( Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and Pseudomonas aeruginosa) and fungi ( Candida albicans, Candida parapsilosis, Aspergillus niger and Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified.

Organic Process Technology Valuation: Cyclohexanone Oxime Syntheses

Three contemporary processes for cyclohexanone oxime synthesis are evaluated in a case study. The case study introduces organic chemistry students to basic cost accounting to determine the most economical technology. Technical and financial aspects of these processes are evaluated with problem-based exercises that may be completed by students either individually or more effectively in groups.

ChemInform Abstract: First Iron‐Catalyzed Synthesis of Oximes from Styrenes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

First iron-catalyzed synthesis of oximes from styrenes

Aryl-substituted olefins react with t-butyl nitrite and sodium borohydride in the presence of iron(ii)phthalocyanine to give oximes in moderate to high yields.

Ultrasound-promoted synthesis of oximes catalyzed by a basic ionic liquid [bmIm]OH

The basic ionic liquid 1-butyl-3-methylimidazolium hydroxide, [bmIm]OH, efficiently catalyzes the condensation reaction of aldehydes and ketones with hydroxylamine hydrochloride under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.

Synthesis of oximes under ultrasound irradiation

The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in 50.7–98.7% yields in EtOH under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.

A Simple Synthesis of Oximes

The conversion of alicyclic and aliphatic carbonyl compounds as well as aromatic aldehydes into the corresponding oximes (up to quantitative yields) was achieved by simply grinding these reactants, hydroxylamine hydrochloride and sodium hydroxide without solvent. However, this procedure was unsuccessful in the case of aromatic ketones. In this case it was necessary to add silica gel as a catalyst.

Solventless Rapid Synthesis of Oxime, Semicarbazone, and Phenylhydrazone Derivatives from Carbonyl Compounds under Microwave Conditions.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of oxime bearing cyclophosphazenes and their reactions with alkyl and acyl halides

Two novel cyclophosphazenes containing oxime groups were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene (2) and hexakis-(4-acetylphenoxy)cyclotriphosphazene (7). The reactions of these oximes with acetyl chloride, chloroacetyl chloride, methyl iodide, propyl chloride, mono- chloroacetone, and 1,4-dichlorobutane were studied. Hexasubstituted compounds were obtained from the reactions of hexakis(4-[(hydroxyimino)methyl]phenoxy)cyclotriphosphazene (3) with acetyl chloride (4) and chloroacetyl chloride (5); however, tetrasubstituted product was obtained from methyl iodide (6). Tetra- and trisubstituted products were obtained from the reactions of hexakis(4-[(1)-N-hydroxyethaneimidoyl]phenoxy)cyclotriphosphazene (8) with acetyl chloride (9) and chloroacetyl chloride (10), respectively. All products were obtained in high yields. Pure and defined product could not be obtained from the reaction of 8 with methyl iodide, and could not be also obtained from the reactions of 3 and 8 with propyl chloride, monochloroacetone, and 1,4-dichlorobuthane. The structures of the compounds were defined by elemental analysis, IR, 1H, 13C, and 31P NMR spectroscopy. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:112–117, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20176