有机化学 ›› 2023, Vol. 43 ›› Issue (12): 4220-4226.DOI: 10.6023/cjoc202304033 上一篇    下一篇

研究论文

N-碘代丁二酰亚胺促进烯基肟的串联氧叠氮化反应: 合成叠氮化异噁唑啉类化合物

刘浩然a,†, 俞骏豪a,†, 曹同阳a, 齐林a,*(), 王力竞a,b,*()   

  1. a 河北大学化学与材料科学学院 河北保定 071002
    b 药物化学与分子诊断教育部重点实验室 河北省化学生物学重点实验室 河北保定 071002
  • 收稿日期:2023-04-25 修回日期:2023-07-17 发布日期:2023-08-16
  • 作者简介:
    共同第一作者
  • 基金资助:
    国家自然科学基金(21702043); 河北省自然科学基金(B2021201035)

N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines

Haoran Liua,†, Junhao Yua,†, Tongyang Caoa, Lin Qia,*(), Lijing Wanga,b,*()   

  1. a College of Chemistry and Materials Science, Hebei University, Baoding, Hebei 071002
    b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, Baoding, Hebei 071002
  • Received:2023-04-25 Revised:2023-07-17 Published:2023-08-16
  • Contact: *E-mail: qilin1013@hbu.edu.cn;wanglj@hbu.edu.cn
  • About author:
    The authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21702043); Hebei Province Natural Science Foundation(B2021201035)

发展了一种N-碘代丁二酰亚胺(NIS)促进下烯基肟和叠氮化钠的氧叠氮化方法, 以良好的收率合成了一系列叠氮化异噁唑啉衍生物. 该反应操作简便且条件温和. 机理研究表明, 该反应可能经历了一个亲电碘环化/亲核取代的串联历程.

关键词: N-碘代丁二酰亚胺(NIS), 烯基肟, 氧叠氮化, 异噁唑啉

A N-iodosuccinimide (NIS)-promoted cascade oxoazidation of alkenyl oximes with NaN3 was developed, and a series of azido isoxazoline derivatives were synthesized in good yields. The reactions are easy to be conducted under mild conditions. The mechanism study shows that the reaction might involve a cascade electrophilic iodocyclization/nucleophilic substitution pathway.

Key words: N-iodosuccinimide (NIS), alkenyl oximes, oxoazidation, isoxazolines