5301-02-0Relevant articles and documents
Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene
Kondrashov, Evgeniy V.,Shatokhina, Nina S.
, p. 1228 - 1232 (2020/01/08)
[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.
Copper-catalysed synthesis of 3,5-disubstituted isoxazoles enabled by pyridinyl benzimidazol (PBI) as a bidentate N-chelating ligand under mild conditions
Khalifeh, Reza,Shahriarpour, Fatemeh,Sharghi, Hashem,Aberi, Mahdi
, p. 813 - 821 (2018/03/01)
In this paper, we introduced pyridinyl benzimidazol (PBI) as an easy-to-handle and bidentate N-chelating ligand that promote clean synthesis of 3,5-disubstituted isoxazoles in the presence of copper acetate as catalyst. This catalytic approach initiates with the hydroxyamination of aldehydes followed by chlorination and then generation of nitrile oxide which subsequently undergoes click-type [3?+?2]-dipolar cycloaddition with alkynes to give isoxazoles. This method provides an alternative green process to construct isoxazole derivatives.
Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link
Chen, Hong-Lei,Wei, Dian,Zhang, Jian-Wu,Li, Cheng-Lin,Yu, Wei,Han, Bing
, p. 2906 - 2910 (2018/05/28)
A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,?- and ?-halo-?,?-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl.
Imidazopyridazine hepatitis C virus polymerase inhibitors. Structure-activity relationship studies and the discovery of a novel, traceless prodrug mechanism
Leivers, Martin,Miller, John F.,Chan, Stephanie A.,Lauchli, Ryan,Liehr, Sebastian,Mo, Wenyan,Ton, Tony,Turner, Elizabeth M.,Youngman, Michael,Falls, J. Greg,Long, Susan,Mathis, Amanda,Walker, Jill
, p. 1964 - 1975 (2014/04/03)
By reducing the basicity of the core heterocycle in a series of HCV NS5B inhibitors, the hERG liability was reduced. The SAR was then systematically explored in order to increase solubility and enable dose escalation while retaining potency. During this e
Processes For The Preparation Of Anti-Viral Compounds And Compositions Containing Them
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Page/Page column 69, (2010/03/02)
Disclosed are processes for the preparation of compounds of formula I and compositions that comprise said compounds of formula I. Also disclosed are processes for the preparation of compounds of formula III and compositions that comprise said compounds of formula III.
ANTI-VIRAL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE
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Page/Page column 62, (2009/03/07)
Disclosed are compounds of Formula (I), pharmaceutically acceptable salts and solvates thereof, compositions thereof, and methods for their preparation and uses for treating viral infections mediated at least in part by a virus in the Flaviviridae family of viruses. (I)
Synthesis and properties of 3-alkyl(aryl)-5-chloromethylisoxazoles
Gadzhily,Aliev
, p. 415 - 418 (2007/10/03)
3-Chloro-2-isothiocyanato-1-propenyl alkyl(aryl) ketones react with hydroxylamine hydrochloride to give 3-alkyl(aryl)-5-chloromethylisoxazole. Treatment of the latter with dimethylamine and ammonium thiocyanate leads to formation of previously unknown 3-alkyl(aryl)-5-dimethylamino(or isothiocyanato)-methylisoxazoles.