1365645-07-3Relevant academic research and scientific papers
Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of Δ2-Isoxazolines from Oximes
Shi, Di,Qin, Hai-Tao,Zhu, Chen,Liu, Feng
supporting information, p. 5084 - 5088 (2015/08/18)
The direct functionalization of an aliphatic C-H bond within a complex molecule through a free-radical pathway is a valuable tool in synthetic chemistry. Herein, we developed an efficient transition-metal-free approach to generate Δ2-isoxazolines from oximes by radical-mediated C(sp3)-H oxidation. Investigation of the mechanism suggested that in the presence of Selectfluor and Bu4NI, the homolysis of the in situ formed O-I bond generated an iminoxyl radical that facilitated subsequent 1,5-H transfer and C(sp3)-H oxidation. The title reaction involves Selectfluor-Bu4NI-mediated C-O bond formation in aqueous media under metal-free conditions. A variety of Δ2-isoxazolines are directly synthesized from oximes by remote intramolecular functionalization of C(sp3)-H bonds.
Synthesis of 3,5-disubstituted isoxazolines and isoxazoles
Ingle,Doshi,Raut,Kadu
, p. 1815 - 1818 (2012/06/15)
2-Acetylthiophene condenses with different aromatic aldehyde in ethanol in the presence of aqueous NaOH to give 1-(2′thienyl)-3-(substituted phenyl)-2-propen-1-one(Ia-e) which reacts with hydroxylamine hydrochloride and aqueous KOH in presence of ethonal medium to give 3-(2′-thienyl)-5- (substituted phenyl)-2-isoxazoline (IIa-e). And 3-(2′-thienyl)- 5-(substituted phenyl)-Δ2-isoxazoline (IIa-e) was dissolved in DMSO. To this catalytic amount of iodine was added. Cooled and diluted with water. The solid thus separated was washed with 20% sodium thiosulphate to give 3-(2′-thienyl)-5-(substituted phenyl)-isoxazole (II′a-e). Characterization and structural elucidation were done on the basis of melting points determination, analytical and spectral studies.
