26218-72-4

Upstream product

• 28123-63-9 4-chlorobenzohydroximoyl chloride 
• 15500-74-0 4-chlorobenzonitrile N-oxide 
• 3848-36-0 4-chlorobenzaldoxime 
• 110-86-1 pyridine 
• 13669-28-8 1-methyl-4-methylene-1-azacyclohexane 
• 2942-58-7 diethyl cyanophosphonate 
• 10403-54-0 phenyl (3-phenyl-2H-aziren-2-yl)methanone 
• 29559-24-8 4-chlorophenylnitromethane 
• 2574-03-0 p-nitrobenzonitrile oxide 
• 73150-59-1 2-(2-chlorophenyl)-1,3-dioxepin-5-ene 
• 698-16-8 benzohydroximoyl chloride 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 24483-06-5 1-isopropyl-3-methyl-1,2-diaza-1,3-butadiene 
• 74903-80-3 (Z)-N-hydroxy-4-chloro-benzenecarboximidoyl chloride 

Downstream Products

• 23766-38-3 3,4-bis(4-chlorophenyl)-1,2,5-oxadiazole 

Relevant academic research and scientific papers

Oxidation of: O -dioxime by (diacetoxyiodo)benzene: Green and mild access to furoxans

Furoxan has been widely used in the field of high energy density materials because of its excellent properties such as high density, high standard enthalpy of formation and high nitrogen content. However, its existing synthesis methods are still restricted by the problems of difficult substrate preparation and manual handling of hazardous reagents. Herein, we disclosed a mild oxidation strategy to efficiently obtain furoxan derivatives starting from readily available o-dioxime substrates. This reaction features high functional group tolerance and easy scale-up, and has excellent regioselectivity for specific nonsymmetric o-dioximes. This method greatly reduces the safety risk and simplifies the operation process, and means that diversified furoxan derivatives can be easily accessed, thus paving the way for the wide application of furoxan derivatives. This journal is

A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide

A library of twenty variously decorated 1,5-disubstituted-(1H-tetrazol-5-yl)methanone oximes was prepared in one single synthetic step exploiting the combination of (Z)-chlorooximes, isocyanides and trimethylsilyl azide. The formal [3+1] cycloaddition between isocyanides and nitrile N-oxides with respect to the [3+1] cycloaddition between isocyanides and azides prevails, while the direct attack of azide onto nitrile N-oxides remains competitive. Finally, an intramolecular cyclization of a (1H-tetrazol-5-yl)methanone oxime to a benzoisoxazole tetrazole is reported for the first time.

Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve (CrO2)

Treatment of aldoximes 1 with Magtrieve (CrO2) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a-u and isoxazoles 6a-q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63-90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed through isolation of the dimerization product furoxane 2a in absence of any dipolarophile. The methodology has been extended to intramolecular nitrile oxide cycloaddition (INOC) reactions to access highly useful chromane derivatives 7-8 (75-80% isolated yields). Magtrieve, as a new reagent for 1,3-DC reactions, has offered excellent substrate generality and at the same time demonstrated tolerance toward sensitive protecting groups and electron-rich functional groups.

Synthesis and Antifungal Activities of Furoxan Derivatives Designed as Novel Fungicide

Furoxan derivatives 3-11 were designed and synthesized as potential fungicides. Symmetrically substituted furoxan derivatives 3a-j were prepared by dimerization of the corresponding nitrile oxide generated from N-hydroxyliminoyl chloride 2 in situ. Further functional group modifications of aldehyde 4, a key intermediate, generated furoxan derivatives 5-11. The fungicidal activities of furoxan derivatives 3-11 were observed over a broad spectrum of plant fungi at 250 ppm.

Cycloadditions of Nitrile Oxides and Nitrones to 4,4-Methylene-1-methylpiperidine: Studies in Regio- and Stereoselectivity

A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine.Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients.X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated ΔHf-values of all possible cycloadducts. - Keywords: 1,3-Dipolar cycloaddition; Nitrile oxide; Nitrone; 4,4-Methylene-1-methylpiperidine; AM1 calculations.

Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (1) is described.The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (>=95percent ?-facial stereoselectivity).

A Convenient Synthesis of Nitrile Oxides from Aldoximes by 1-Chlorobenzotriazole

Nitrile oxides can be conveniently prepared from aldoximes utilizing 1-chlorobenzotriazole in dichloromethane.The reaction and work-up procedures are simple and the isolated yields high.

Organic Curing Agents for Polysulfide Sealants. III A Mechanistic Interpretation of the Thermal Degradation of Nitrile Oxide-Cured Polysulfide Sealants

Sealants obtained by cure of polysulfide liquid polymers with aryl bis(nitrile oxides) possess the thiohydroximic acid ester structural feature.Unexpectedly these materials were found to exhibit poor thermal stability: when heated at 60 deg they soften wi

Isoxazolinyldioxepins. Part 1. Structure-Reactivity Studies of the Hydrolysis of Oxazolinyldioxepin Derivatives

The preparation and acid catalyzed hydrolysis of a number of isoxazolinyldioxepins is reported.Individual diastereoisomer pairs were isolated by column chromatography and shown to differ significantly in their hydrolytic stability at acidic pH.The crystal structures of one diastereoisomer pair reveal that conformational differences induce a selective stereoelectronic effect at the acetal centre of the more hydrolytically labile isomer, while the less labile isomer shows no such selectivity.

Crossed Bisadducts in the Reaction of Pyridine with Two Different Nitrile Oxides.

Bisadducts of some aromatic nitrile oxides to pyridine are described.Crossed adducts are formed by exposure of pyridine to a couple of different nitrile oxides.