53215-16-0Relevant academic research and scientific papers
Synthesis of 4-Nitroisoxazoles via NO/NO2 -Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones
Averina, Elena B.,Grishin, Yuri K.,Kurova, Anastasiya V.,Kuznetsova, Tamara S.,Rybakov, Victor B.,Sadovnikov, Kirill S.,Sedenkova, Kseniya N.,Vasilenko, Dmitry A.,Volkova, Yulia A.
, p. 1398 - 1406 (2020/04/27)
A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted α,β-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t -BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.
Trifluoromethylation of aromatic isoxazoles: Regio- and diastereoselective route to 5-trifluoromethyl-2-isoxazolines
Kawai, Hiroyuki,Tachi, Kentaro,Tokunaga, Etsuko,Shiro, Motoo,Shibata, Norio
supporting information; scheme or table, p. 7803 - 7806 (2011/10/05)
It all adds up: The activation of aromatic isoxazoles with a nitro group at the 4-position has enabled the first regio- and diastereoselective trifluoromethylation at the 5-position of isoxazoles by nucleophilic addition using Me3SiCF3 (see scheme; DMF=N,N′- dimethylformamide). The process was demonstrated with a broad range of 3,5-aromatic, heteroaromatic and aliphatic substrates.
Preparation of 4-Bromo-1-hydroxypyrazole 2-Oxides by Nitrosation of α-Bromo-α,β-unsaturated Ketoximes
Hansen, John F.,Easter, John A.,Eckert, David A.,Hunt, Karen J.,Little, David A.
, p. 281 - 286 (2007/10/02)
Nitrosation of the oximes of 3-bromo-3-penten-2-one, 3-bromo-4-phenyl-3-buten-2-one, and 2-bromo-1,3-diphenyl-2-propen-1-one using sodium nitrite in acetic acid gave low yields of 4-pyrazolone 1,2-dioxides.Nitrosation using butyl nitrite in the presence of copper(II) sulfate and pyridine in aqueous ethanol produced insoluble copper complexes from which 3,5-dimethyl-, 3-methyl-5-phenyl-, and 3,5-diphenyl-4-bromo-1-hydroxypyrazole 2-oxides could be liberated by treatment with dilute potassium hydroxide, filtration, and acidification of the filtrate.High yields wereobtained with the first two oximes, but, presumably due to unfavorable stereochemistry of the oxime, the diphenyl derivative gave a lower yield of the complex, accompanied by 4-bromo- and 4-nitro-3,5-diphenylisoxazole and 4-oximino-3,5-diphenyl-4,5-dihydroisoxazole.
SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. PART XX. STUDIES ON THE THERMOLYSIS OF REGIO AND STEREOISOMERIC DIARYLNITRO-Δ2-ISOXAZOLINES
Baranski, Andrzej,Cholewka, Elzbieta
, p. 483 - 494 (2007/10/02)
Thermolysis of stereoisomeric 3,5-diaryl-4-nitro-Δ2-isoxazolines 1, 3, depending on the applied solvent, leads to 3,5-diarylisoxazoles 4 or mixtures of 3,5-diarylisoxazoles 4 and 3,5-diaryl-4-nitroisoxazoles 6.Under similar conditions, 3,4-diar
SYNTHESIS AND PROPERTIES OF 4-HALO-4-NITROISOXAZOLINES
Trusova, T. V.,Malyuta, N. G.,Khisamutdinov, G. Kh.
, p. 1187 - 1190 (2007/10/02)
Chloro-, bromo-, and iodo-derivatives of substituted 4-nitroisoxazolines have been synthesized by direct halogenation of the latter, and their chemical properties have been studied, among them their conversion to 4-nitroisoxazole derivatives by eliminatio
SYNTHESIS AND PROPERTIES OF AZOLS AND THEIR DERIVATIVES. PART XII. REGIO- AND STEREOCHEMISTRY IN CYCLOADDITION REACTIONS OF β-NITROSTYRENES WITH BENZONITRILE n-OXIDE
Baranski, Andrzej
, p. 107 - 119 (2007/10/02)
1,3-Dipolar cycloaddition of trans-β-nitrostyrenes 1a-d to benzonitrile N-oxide 2 has been investigated.It was found that regioisomeric 4,5-dihydro-1,2-oxazoles were formed as primary products due to two possible orientations of reactants in the transitio
SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 10. SYNTHESIS OF 3,5-DIARYL-4-NITROISOXAZOLES
Baranski, A.
, p. 153 - 156 (2007/10/02)
A method was proposed for the synthesis of 3,5-diaryl-4-nitroisoxazoles entailing the bromination of potassium salts of the corresponding 3,5-diaryl-Δ2-isoxazolinyl-4-nitronic acids.The method may be used for the conversions of both the trans and cis isomers of 3,5-disubstituted 4-nitro-Δ2-isoxazolines.
