Halonium Ion Mediated Synthesis of 2-Halomethylene-3-oxoketoxime Derivatives from Isoxazoline N-Oxides
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- 作者：Mustafa J. Raihan ; R. R. Rajawinslin ; Veerababurao Kavala ; Chun-Wei Kuo ; Ting-Shen Kuo ; Chiu-Hui He ; Hsiu-Ni Huang ; Ching-Fa Yao
- 刊名：Journal of Organic Chemistry
- 出版年：2013
- 出版时间：September 6, 2013
- 年：2013
- 卷：78
- 期：17
- 页码：8872-8879
- 全文大小：415K
- 年卷期：v.78,no.17(September 6, 2013)
- ISSN：1520-6904
文摘
A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated synthesis of novel 2-halomethylene-3-oxoketoximes via one-pot halogenation/oxidation of isoxazoline N-oxide derivatives is described here. The keto functionality of 3-ketoximes was selectively reduced by lithiumaluminum hydride to synthesize an unprecedented type of Baylis鈥揌illman oxime, which underwent N鈥揙 coupling to produce new isoxazoline N-oxide derivative.