1011-38-7Relevant articles and documents
An expeditious synthesis of isoxazoline using cetyltrimethylammonium cerium nitrate: A phase transferring oxidative 1,3-dipolar cycloaddition
Kumar, Parvin,Kumar, Ashwani
, p. 1287 - 1290 (2010)
An expeditious and effective method for synthesis of isoxazoline from aldoximes and activated alkenes using cetyltrimethylammonium cerium nitrate at room temperature is described. Reaction was completed within short time period in high yields at room temp
Electrochemical Synthesis of Isoxazolines: Method and Mechanism
Holman, Samuel D. L.,Wills, Alfie G.,Fazakerley, Neal J.,Poole, Darren L.,Coe, Diane M.,Berlouis, Leonard A.,Reid, Marc
, (2022/02/19)
An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline in an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modelling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesised involvement of closed shell [3+2] cycloaddition pathways.
Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles from olefinic azlactones
Lin, Yifan,Zhang, Ke,Gao, Mingchun,Jiang, Zheyi,Liu, Jiajie,Ma, Yurui,Wang, Haoyu,Tan, Qitao,Xiao, Junjie,Xu, Bin
supporting information, p. 5509 - 5513 (2019/06/14)
A copper nitrate-mediated [2 + 2 + 1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting 3-aryl substituted isoxazolines and isoxazoles through CC bond cleavage. Copper nitrate is employed as a reaction promoter and precursor of nitrile oxides. The given approach features a new mode of cycloaddition from olefinic azlactones, copper nitrate and unsaturated compounds with wide substrate scope, good functional group tolerance and operational simplicity.
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.