20822-00-8Relevant articles and documents
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Barnes et al.
, p. 276 (1954)
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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.).
