1064075-16-6Relevant academic research and scientific papers
[2 + 2 + 1] Cycloaddition ofN-tosylhydrazones,tert-butyl nitrite and alkenes: a general and practical access to isoxazolines
Bao, Xiaoguang,Cheng, Xionglve,Jiang, Gangzhong,Jin, Feng,Li, Xingxing,Ma, Liang,Tao, Suyan,Wan, Xiaobing,Yang, Jinwei
, p. 9823 - 9830 (2021/07/28)
N-Tosylhydrazones have proven to be versatile synthons over the past several decades. However, to our knowledge, the construction of isoxazolines based onN-tosylhydrazones has not been examined. Herein, we report the first demonstrations of [2 + 2 + 1] cycloaddition reactions that allow the facile synthesis of isoxazolines, employingN-tosylhydrazones,tert-butyl nitrite (TBN) and alkenes as reactants. This process represents a new type of cycloaddition reaction with a distinct mechanism that does not involve the participation of nitrile oxides. This approach is both general and practical and exhibits a wide substrate scope, nearly universal functional group compatibility, tolerance of moisture and air, the potential for functionalization of complex bioactive molecules and is readily scaled up. Both control experiments and theoretical calculations indicate that this transformation proceedsviathein situgeneration of a nitronate from the coupling ofN-tosylhydrazone and TBN, followed by cycloaddition with an alkene and subsequent elimination of atert-butyloxy group to give the desired isoxazoline.
Simple preparation method of isoxazoline
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Paragraph 0020-0034, (2021/07/24)
The invention discloses a simple preparation method of isoxazoline. The simple preparation method is characterized in that a series of isoxazoline compounds are efficiently synthesized by using aldehyde, p-toluenesulfonhydrazide, olefin and tert-butyl nit
Synthesis and diverse general oxidative cyclization catalysis of high-valent MoVIO2(HL) to ubiquitous heterocycles and their chiral analogues with high selectivity
Pramanik, Nabyendu,Sarkar, Satinath,Roy, Dipanwita,Debnath, Sudipto,Ghosh, Sukla,Khamarui, Saikat,Maiti, Dilip K.
, p. 101959 - 101964 (2015/12/08)
The first synthesis and diverse oxidative cyclization catalysis properties of high-valent MoVI-triazole are demonstrated towards highly selective construction of benzimidazoles, benzothiazoles, isoxazolines, isoxazoles and their chiral analogue
Generation of nitrile oxides under nanometer micelles built in neutral aqueous media: Synthesis of novel glycal-based chiral synthons and optically pure 2,8-dioxabicyclo[4.4.0]decene core
Chatterjee, Nirbhik,Pandit, Palash,Halder, Samiran,Patra, Amarendra,Maiti, Dilip K.
, p. 7775 - 7778 (2008/12/22)
(Chemical Equation Presented) A highly efficient strategy for chemoselective oxidation of aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media is reported. Their in situ intermolecular 1,3-dipolar cycloaddition (1,3-DC) with olefins in nanometer aqueous micelles occurs with improved stereoselectivity and acceleration of reaction rate toward synthesis of new chiral synthons, 3-(2′-C-3′,4′,6′-tri-O- benzylglycal)-Δ2-isoxazolines and others. Construction of optically pure 2,8-dioxabicyclo[4.4.0]decene skeleta is performed by this green approach, and the stereochemistry of the new chiral center is predicted by B3LYP density functional theory.
