54606-00-7Relevant academic research and scientific papers
An efficient synthesis of 2-isoxazolines from α-haloketone oximes and dimethyl sulfonium salts
Zhao, Sen,Wang, Hang,Sun, Shaofa,Guo, Haibing,Chen, Zhiyu,Wang, Jian,Wang, Lu,Liang, Steven,Wang, Gangqiang
supporting information, p. 382 - 385 (2019/01/04)
2-Isoxazolines were synthesized efficiently from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a rang
Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles
Svejstrup, Thomas D.,Zawodny, Wojciech,Douglas, James J.,Bidgeli, Damon,Sheikh, Nadeem S.,Leonori, Daniele
, p. 12302 - 12305 (2016/10/22)
Visible-light photoredox catalysis enables the synthesis of biologically relevant isoxazolines and isoxazoles from hydroxyimino acids. The process shows broad functional group compatibility and mechanistic and computational studies support a visible-light-mediated generation of nitrile oxides by two sequential oxidative single electron transfer processes.
3-Aryl-5-vinyl-2-isoxazolines and 3-aryl-5-vinylisoxazoles from aryl nitrile oxides and methyl vinyl ketone lithium enolate: Reaction limits and synthetic utility exploitation
Salomone, Antonio,Scilimati, Antonio,Vitale, Paola
, p. 807 - 816 (2015/03/14)
3-Aryl-5-hydroxy-5-vinyl-2-isoxazolines were synthesized by reacting aryl nitrile oxides with the lithium enolate of methyl vinyl ketone (MVK) at-78 °C. Fair to good yields are obtained in the case of aryl nitrile oxides bearing electron-withdrawing group
3-aryl-5-vinyl-2-isoxazolines and 3-aryl-5-vinylisoxazoles from aryl nitrile oxides and methyl vinyl ketone lithium enolate: Reaction limits and synthetic utility exploitation
Salomone, Antonio,Scilimati, Antonio,Vitale, Paola
, (2015/02/02)
3-Aryl-5-hydroxy-5-vinyl-2-isoxazolines were synthesized by reacting aryl nitrile oxides with the lithium enolate of methyl vinyl ketone (MVK) at -78 °C. Fair to good yields are obtained in the case of aryl nitrile oxides bearing electron-withdrawing grou
2-Isoxazolines with an electron-acceptor substituent at C(5) in reactions with nucleophilic reagents
Koroleva,Bondar,Katok,Chekanov,Chernikhova
, p. 362 - 369 (2008/09/21)
Depending on the substituent at position 5 of the heterocycle, reaction of 2-isoxazolines with K-selectride, molybdenum hexacarbonyl, dimsyl sodium, and butyl lithium gave 1,3-cyclo-decomposition, aromatization of the isoxazoline ring, or reduction of the functional groups in the substituted isoxazolines.
5-Hydroxy-3-phenyl-5-vinyl-2-isoxazoline and 3-phenyl-5-vinylisoxazole: Synthesis and reactivity
Di Nunno, Leonardo,Scilimati, Antonio,Vitale, Paola
, p. 11270 - 11278 (2007/10/03)
5-Hydroxy-3-phenyl-5-vinyl-2-isoxazoline has been synthesized by reacting benzonitrile oxide with the enolate ion of methyl vinyl ketone. From 5-hydroxy-5-vinyl-2-isoxazoline, 5-vinylisoxazole was then quantitatively obtained by dehydration-aromatization
1,3-Dipolar cycloadditions of benzonitrile oxide with various dipolarophiles in aqueous solutions. A kinetic study
Van Mersbergen, Dick,Wijnen, Jan W.,Engberts, Jan B. F. N.
, p. 8801 - 8805 (2007/10/03)
The second-order rate constants for the 1,3-dipolar cycloaddition of benzonitrile oxide (1) with various dipolarophiles (2a-e) were determined in aqueous media and in organic solvents to gain more insight into the influence of an aqueous medium on pericyclic reactions. 1,3-Dipolar cycloadditions with electron-poor dipolarophiles are accelerated in water and protic solvents, whereas an aqueous medium has no special effect when electron-poor dipolarophiles are involved. These observations can be explained using frontier molecular orbital theory. In all cases, enforced hydrophobic interactions promote the reaction. These results are supported by kinetic experiments in waterethanol mixtures. Sodium dodecyl sulfate micelles accelerate the cycloaddition of 1 with both electron-rich and electron-poor dipolarophiles. More than for other systems, the present results show that hydrogen bonding and hydrophobic interactions can either cooperate or counteract each other in determining the kinetic medium effects in aqueous solutions.
A Highly Effective Quenching Method of 1,3-Dipolar Cycloadditions of Nitrile Oxides or Nitrile Oxide/Lewis Acid Complexes by Use of 2-Propenyloxymagnesium Bromide
Kanemasa, Shuji,Nishiuchi, Masaki
, p. 4011 - 4014 (2007/10/02)
2-Propenyloxymagnesium bromide, readily prepared by treating 2-propen-1-ol with EtMgBr, is a highly effective quencher of nitrile oxide cycloadditions since this alkoxide is much more reactive to nitrile oxides than any other ever known dipolarophiles of
Nucleophilic Additions to and Reductions of 5-Formyl- and 5-Acyl-2-isoxazolines (4,5-Dihydroisoxazoles): A Stereoselective Route to β,γ-Dihydroxy Ketones
Curran, Dennis P.,Zhang, Jiancun
, p. 2613 - 2625 (2007/10/02)
Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (>95:5) selectivities.Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct ad
Some Acylations of 3-Phenyl and 3-Mesityl-4,5-dihydroisoxazoles
Corsaro, Antonino,Chiacchio, Ugo,Perrini, Giancarlo,Caramella, Pierluigi,Albini, Franca Marinone
, p. 1691 - 1699 (2007/10/02)
A study on the acetylation and benzoylation of title compounds by quenching the corresponding 4-carbanions with acyl chlorides or esters is reported.The obtained ketones are formed as minor regioisomeric adducts in the cycloadditions of benzo and mesitoni
