7063-98-1Relevant academic research and scientific papers
Transition-Metal-Free Multicomponent Approach to Stereoenriched Cyclopentyl-isoxazoles through C?C Bond Cleavage
Subramanian, Parthasarathi,Kaliappan, Krishna P.
, p. 2031 - 2039 (2018)
An efficient multicomponent reaction for the synthesis of stereoenriched cyclopentyl-isoxazoles from camphor-derived α-oximes, alkynes, and MeOH is reported. Our method involved a series of cascade transformations, including the in situ generation of an IIII catalyst, which catalyzed the addition of MeOH to a sterically hindered ketone. Oxidation of the oxime, and rearrangement of the α-hydroxyiminium ion generated a nitrile oxide in situ, which, upon [3+2] cycloaddition reaction with an alkyne, delivered the regioselective product. This reaction was very selective for the syn-oxime. This multicomponent approach was also extended to the synthesis of a new glycoconjugate, camphoric ester-isoxazole C-galactoside.
Synthesis of 3-Acyl-Isoxazoles via Radical 5-endo trig Cyclization of β,γ-Unsaturated Ketones with NaNO2
Chen, Dengfeng,Huang, Shenlin,Jiang, Ping,Wang, Yaming,Zheng, Yu
, (2022/02/07)
Here we report a facile cyclization reaction of β,γ-unsaturated ketones with NaNO2 under mild conditions to construct 3-acyl-isoxazoles. This transformation is realized via nitrosation of the activated methylene, radical 5-endo trig cyclization
Synthetic Diversity from a Versatile and Radical Nitrating Reagent
Zhang, Kun,Jelier, Benson,Passera, Alessandro,Jeschke, Gunnar,Katayev, Dmitry
supporting information, p. 12929 - 12939 (2019/09/17)
We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
A convenient synthetic method of isoxazole derivatives using copper(II) nitrate
Itoh, Ken-Ichi,Aoyama, Tadashi,Satoh, Hiroaki,Hasegawa, Kenta,Meguro, Natsumi,Horiuchi, Akira C.,Takido, Toshio,Kodomari, Mitsuo
, p. 1473 - 1482 (2014/07/07)
3-Acetylisoxazoles were synthesized by the reaction of alkenes or alkynes in acetone as solvent with copper(II) nitrate and formic acid. In the case of ethyl acetate as solvent, 3-benzoylisoxazoles were yielded by the reaction of alkynes and acetophenone
The branch part and delivery system, the catheter assembly
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, (2007/10/08)
A catheter assembly including a side branch locator that is moveable between a retracted position within a main vessel of a vessel bifurcation, and an extended position wherein a distal end of the side branch locator extends into a branch vessel of the vessel bifurcation. The side branch locator includes a first end fixed relative to a portion of the catheter assembly that remains in the main vessel. A second end of the side branch locator is moveable between the retracted and extended positions. The catheter assembly can include a moveable sheath that holds the side branch locator in the retracted position. The catheter assembly can further include a stent having a lateral branch opening through which the side branch locator extends.
Reactivity of the ester group attached isoxazoline, benzisoxazole, and isoxazole: A facial preparation of 3-acyl-substituted these heterocycles
Murai, Kenichi,Miyazaki, Shuji,Fujioka, Hiromichi
, p. 3746 - 3749 (2012/10/07)
A facile preparation of 3-acyl-substituted isoxazolines, benzisoxazoles, and isoxazoles from the corresponding 3-carboxylate esters is described. The process, involving reaction of the ester derivative of 3-carboxylic acid substituted heterocycles with Gr
1,4-Diazabicyclo[2.2.2]octane (DABCO) as an efficient reagent for the synthesis of isoxazole derivatives from primary nitro compounds and dipolarophiles: The role of the base
Cecchi, Luca,De Sarlo, Francesco,Machetti, Fabrizio
, p. 4852 - 4860 (2007/10/03)
The dehydration of primary nitro compounds can be performed by bases in the presence of dipolarophiles. The reactivity of several tertiary amines or azaheteroaromatic compounds containing one or two basic centres is shown to be related to the ability of t
A convenient and efficient one-pot synthesis of 3-acylisoxazoles using iron(III) salts
Itoh, Ken-Ichi,Sakamaki, Hiroshi,Nakazato, Noriko,Horiuchi, Atsuo,Horn, Ernst,Horiuchi, C. Akira
, p. 3541 - 3548 (2007/10/03)
3-Acylisoxazoles were synthesized by the reaction of alkenes or alkynes with ketones (acetone or acetophenone), as both a reagent and the solvent, by three methods: iron(III) nitrate under reflux, iron(III) salt-nitrogen dioxide (NO2) at room temperature,
Pharmacochemistry of the furoxan ring: Recent developments
Calvino,Di Stilo,Fruttero,Gasco,Sorba,Gasco
, p. 321 - 334 (2007/10/02)
In the present work recent results obtained in the pharmacochemistry of the furoxan system are reported. In particular, after a brief description of the salient points of the furoxan chemistry, the synthesis and the properties of a series of Nifedipine and Prazosin analogues, containing this heterocyclic system, are described. Since we observed that a few furoxan derivatives are able to elicit both a dose-dependent rise in platelet cGMP levels and to promote a dose-dependent inhibition of AA-induced [Ca++] rise, and that many substituted furoxans show potent vasodilating and antiaggregatory activity, the possibility of using the furoxan system as a lead in the design of new vasodilators is also discussed.
