60579-19-3Relevant academic research and scientific papers
TEMPO-Mediated Selective Synthesis of Isoxazolines, 5-Hydroxy-2-isoxazolines, and Isoxazoles via Aliphatic δ-C(sp3)-H Bond Oxidation of Oximes
Mondal, Santanu,Biswas, Sourabh,Ghosh, Krishna Gopal,Sureshkumar, Devarajulu
, p. 2439 - 2446 (2021/08/03)
Selective synthesis of three different bioactive heterocycles; isoxazolines, 5-hydroxy-2-isoxazolines and isoxazoles from the same starting material using TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) as a radical initiator is reported. Selectivity was achi
Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving CC bond Oxidative Cleavage: Entry to 3-Aryl-?2-isoxazolines
Wang, Cheng-Yong,Wang, Cheng-Yong,Teng, Fan,Li, Yang,Li, Jin-Heng,Li, Jin-Heng,Li, Jin-Heng
supporting information, p. 4250 - 4254 (2020/06/05)
A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the CC bond promoted by cooperative Zn(OTf)2, KOAc, and 4 ? MS for producing 3-aryl δ2-isoxazolines is reported. Mechanistic s
Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization
Cheng, Jiaxin,Yang, Ze,Li, Yuansheng,Xi, Yulan,Sun, Qiu,He, Ling
, p. 2385 - 2393 (2018/05/28)
A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO 2 /C-N bond formation is achieved in sequence in the reaction system.
Base-Promoted [3+2]-Annulation of Oxime Esters and Aldehydes for Rapid Isoxazoline Formation
Huang, Huawen,Li, Feifei,Xu, Zhenhua,Cai, Jinhui,Ji, Xiaochen,Deng, Guo-Jun
supporting information, p. 3102 - 3107 (2017/09/13)
A base-promoted [3+2]-annulation of ketoxime esters and aldehydes is disclosed for the facile and rapid synthesis of 3,5-disubstituted and 3,4,5-trisubstituted isoxazolines. The key to our success is the pivalate leaving group of the oxime substrates, combined with cesium carbonate as promoter. This chemistry allows the assembly of a vast array of isoxazoline derivatives under simple base conditions in a method complementary to the classic isoxazoline formation via [3+2]-dipolar cycloaddition of nitrile oxides and olefins. It also represents a new reaction pattern involving electrophilic amination/N–O bond substitution. (Figure presented.).
3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof
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Paragraph 0130, (2017/08/31)
The invention relates to 3,4,5-trisubstituted-4,5-dihydroisoxazole, a derivative and a synthetic method and an application thereof. The invention mainly relates to a synthetic method of an isoxazoline compound. With adoption of a technical scheme that an aldehyde compound and oxime ester are converted into isoxazoline and the derivative thereof by taking an organic solvent as a solvent under the action of alkali without using a catalyst, the synthetic method solves the problem that an existing synthetic method of the isoxazoline compound is complicated in synthetic step, is accomplished by adopting multiple steps, and also needs a metal catalyst, a chemically equivalent metal oxidant or a peroxide. The atom economy is kept to the extreme extent; the isoxazoline compound has a stable molecular structure and an excellent chemical property, and molecular slices and compound segments contain rich contents with biological activity and pharmacological activity. The isoxazoline compound also has the characteristics of being simple in reaction system, mild in reaction condition, relatively less in reaction equipment, simple in experimental operation, wide in source of materials, high in yield, easy for expansion of user and application, relatively high in utilization value of product and expectable in market commercial prospect.
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
supporting information, 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.
Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes
Yoshimura, Akira,Middleton, Kyle R.,Todora, Anthony D.,Kastern, Brent J.,Koski, Steven R.,Maskaev, Andrey V.,Zhdankin, Viktor V.
, p. 4010 - 4013 (2013/09/02)
Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.
Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant
Yoshimura, Akira,Zhu, Chenjie,Middleton, Kyle R.,Todora, Anthony D.,Kastern, Brent J.,Maskaev, Andrey V.,Zhdankin, Viktor V.
supporting information, p. 4800 - 4802 (2013/06/05)
Isoxazolines can be efficiently synthesized in good yields via a hypoiodite mediated catalytic oxidative cyclization of aldoximes and alkenes. This reaction involves active iodine species generated in situ from catalytic amounts of KI and Oxone.
Synthesis of some 3,5-diaryl-2-isoxazoline derivatives in ionic liquids media
Safaei-Ghomi, Javad,Ghasemzadeh, Mohammad Ali
, p. 733 - 739 (2012/09/22)
Biologically active isoxazoline derivatives were efficiently synthesized in excellent yields and in smaller reaction times using mild, effective and environmentally friendly butylmethylimidazolium bromide as the solvent and catalyst. By use of this cataly
Ba(OH)2 AS THE CATALYST IN ORGANIC REACTIONS-PART X-REACTION OF CHALCONE WITH HYDROXYLAMINE
Sinisterra, J. V.,Marinas, J. M.
, p. 293 - 302 (2007/10/02)
The reaction of several chalcones with hydroxylamine has been studied.A systematic catalytic study of the synthetic process has been accomplished.The different experimental conditions have been studied.The process catalyzed in the homogeneous phase gives
