26218-73-5Relevant articles and documents
Oxidation of: O -dioxime by (diacetoxyiodo)benzene: Green and mild access to furoxans
He, Chunlin,Pang, Siping,Zhang, Qi,Zhang, Xun,Zhao, Cheng
supporting information, p. 1489 - 1493 (2022/01/31)
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
Synthesis of alkynyl furoxans. Rare carbon-carbon bond-forming reaction on a furoxan ring
Matsubara, Ryosuke,Eguchi, Shuhei,Ando, Akihiro,Hayashi, Masahiko
, p. 1965 - 1969 (2017/03/11)
A rare carbon-carbon-bond forming reaction on a furoxan ring has been developed. The nucleophilic aromatic substitution (SNAr) reaction of 4-nitrofuroxans with alkynyl lithium proceeded with high yields, which enabled the first practical synthesis of both alkynyl furoxan regioisomers. Due to the versatility of the alkyne functional group, various derivatizations of the carbon-carbon triple bond in the afforded products were possible. Thus, this developed method is a convergent approach to a wide spectrum of carbon-substituted furoxans.
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
Al-Timari, Usama A. R.,Fisera, Lubor
, p. 121 - 127 (2007/10/02)
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).
Isoxazolinyldioxepins. Part 1. Structure-Reactivity Studies of the Hydrolysis of Oxazolinyldioxepin Derivatives
Camilleri, Patrick,Munro, David,Weaver, Karen,Williams, David J.,Rzepa, Henry S.,Slawin, Alexandra M. Z.
, p. 1929 - 1934 (2007/10/02)
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.
Albini, Franca Marinone,Franco, Rita De,Bandiera, Tiziano,Caramella, Pierluigi,Corsaro, Antonino,Perrini, Giancarlo
, p. 757 - 761 (2007/10/02)
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.
Formation of 4-Benzamidoisoxazole Derivatives
Zen, Shonosuke,Harada, Kazuho,Nakamura, Hikaru,Iitaka, Yoichi
, p. 2881 - 2884 (2007/10/02)
The titled compounds (3) were synthesized by the reaction of nitrile oxides with 1-azirines and also the reaction of aliphatic nitro compounds with dibenzoylmethane derivatives in the presence of acetyl chloride and sodium methoxide.The structure of 3 was
Dialkyl (3-Aryl-1,2,4-oxadiazol-5-yl)phosphonates: Synthesis and Thermal Behavior - Evidence for Monomeric Alkyl Metaphosphate
Das, Sushanta K.,Balasubrahmanyam, S. N.
, p. 4232 - 4236 (2007/10/02)
Dialkyl (3-aryl-1,2,4-oxadiazol-5-yl)phosphonates 6a-h have been obtained by 1,3-dipolar cycloaddition of arenenitrile oxides 5a-f to dialkyl phosphorocyanidates (4a and 4b) in yields ranging between 30percent and 58percent.A standardized method for obtaining cyanidates 4a and 4b has been established.The diethyl thiophosphorocyanidate (4c) is less reactive than 4a and 4b, only the 3-(4'-nitrophenyl) derivative 6i being obtainable.While the IR and NMR spectra of 6a-6i were unexceptional, their UV spectra showed evidence of conjugative interaction in high degrees between the phosphonate and heterocyclic moieties as well as a varying conjugative interaction between the heterocyclic and aryl moieties.The oxadiazoles 6a-h are thermally labile and yield trialkyl phosphates 7 as the only identifiable products.A mechanism based on the intermediacy of monomeric alkyl metaphosphate 11 in the formation of trialkyl phosphate was postulated, and supportive evidence in the form of trapping the metaphosphate with acetophenone has been obtained.
