1006-65-1Relevant academic research and scientific papers
Substituent effects on 15N and 13C NMR chemical shifts of 3-phenylisoxazoles: A theoretical and spectroscopic study
Schofield, Mark H.,Sorel, Marie-Adele,Manalansan, Ryan J.,Richardson, David P.,Markgraf, J. Hodge
, p. 851 - 855 (2006)
The synthesis and assignment of 15N and 13C NMR signals of the isoxazole ring in a series of parasubstituted 3-phenyl derivatives are reported. DFT calculations of 15N and 13C chemical shifts are presented and c
Synthesis of 3-Vinylisoxazole by a Nitrile Oxide Cycloaddition/Diels-Alder Cycloreversion Pathway
Ambler, Philip W.,Paton, R. Michael,Tout, Jaki M.
, p. 2661 - 2662 (1994)
3-Vinylisoxazole is prepared by a sequence involving cycloaddition of acrylonitrile oxide, generated by dehydration of 1-nitropropene, to norbornadiene followed by Diels-Alder cycloreversion of the resulting 2-isoxazoline under flash vacuum pyrolysis cond
1,3-Dipolar cycloaddition reaction of substituted trimethylstannylacetylenes with nitrile oxides
Sakamoto,Uchiyama,Kondo,Yamanaka
, p. 478 - 480 (1993)
1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene
Generation of an 4-Isoxazolyl Anion Species: Facile Access to Multifunctionalized Isoxazoles
Morita, Taiki,Fuse, Shinichiro,Nakamura, Hiroyuki
, p. 13580 - 13584 (2016)
A direct functionalization of unsubstituted isoxazole (1) was achieved by generation of 4-isoxazolyl anion species (3). An efficient 4-iodination of isoxazole and halogen–metal exchange reaction using a turbo Grignard reagent (iPrMgCl? LiCl) were essentia
Transition metal catalyzed ring opening reactions of 2-phenyl-3-vinyl substituted 2H-azirines
Padwa, Albert,Stengel, Thomas
, p. 5991 - 5993 (2004)
Treatment of 2-phenyl-3-vinyl-substituted 2H-azirines with Grubbs' catalyst induces a clean rearrangement and affords products derived from carbon-nitrogen bond cleavage of the 2H-azirine ring. However, when the reaction was carried out using Wilkinson's catalyst in an alcoholic solvent, the only product obtained in high yield corresponded to an α,β-unsaturated oxime.
Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate
Kumar, Pravin,Kapur, Manmohan
supporting information, p. 5855 - 5860 (2020/07/30)
An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.
Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles
Kumar, Pravin,Kapur, Manmohan
supporting information, p. 2134 - 2138 (2019/03/26)
High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.
Preparation method of isoxazole derivative
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Paragraph 0054-0059, (2019/12/02)
The invention relates to a preparation method of an isoxazole derivative, which comprises the following steps of mixing an propargyl alcohol derivative, a halogen source, an acid and a solvent, and heating to react; adding the hydroxylamine into the react
Method for converting lignin into isoxazole and aromatic nitrile
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Paragraph 0051; 0052; 0064, (2019/07/04)
The present invention relates to a method for obtaining isoxazole and aromatic nitrile from a lignin model and pre-oxidized birch lignin. The method is characterized in that hydroxylamine hydrochloride and a beta-O-4 model compound containing ketone in the benzyl position, which are used as reaction substrates, undergo oximation condensation Cbeta-O bond fracture under the action of magnesium andother additives to prepare the isoxazole compound, and undergo oximation rearrangement Calpha-Cbeta bond fracture the action of magnesium and other additives to prepare the fragrant nitrile compound.The method can be applied to the conversion of pre-oxidized lignin into the isoxazole and aromatic nitrile. The preparation method comprises the following steps: mixing the beta-O-4 model compound orpre-oxidized birch lignin, hydroxylamine hydrochloride and the additives in an alcohol solvent, adding the obtained mixture into a pressure-resistant container, replacing air in the container with nitrogen, sealing the container, and stirring the mixture at 120 DEG C for 8-12 h to obtain the products isoxazole and aromatic nitrile. The method realizes the obtaining of nitrogen-containing compoundssuch as isoxazole and aromatic nitrile from lignin for the first time, and the reaction process is simple and controllable, and is easy to operate.
Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles
Jeyaveeran,Praveen, Chandrasekar,Arun,M Prince,Perumal
, p. 73 - 83 (2016/02/09)
The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, β-acetylenic oximes and α, β-acetylenic hydrazones is t
