Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

被引:7
作者
Cheng, Jiaxin [1 ]
Yang, Ze [1 ]
Li, Yuansheng [1 ]
Xi, Yulan [1 ]
Sun, Qiu [2 ]
He, Ling [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, West China Med Ctr, Chengdu 610041, Sichuan, Peoples R China
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 12期
基金
美国国家科学基金会;
关键词
isoxazolines; isoxazoles; desulfurization; radical cyclization; tandem reaction; AEROBIC OXIDATIVE AMINATION; C-H BONDS; NITRILE OXIDES; INTERMOLECULAR AMINATION; REGIOSELECTIVE SYNTHESIS; OXIMES; ALKENES; AMIDATION; EFFICIENT; POLYMERIZATION;
D O I
10.1055/s-0037-1609480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:2385 / 2393
页数:9
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