Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides

Mustafa J. Raihan, R. R. Rajawinslin, Veerababurao Kavala, Chun Wei Kuo, Ting Shen Kuo, Chiu Hui He, Hsiu Ni Huang, Ching Fa Yao

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Abstract

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-Hillman oxime, which underwent N-O coupling to produce new isoxazoline N-oxide derivative.

Original languageEnglish
Pages (from-to)8872-8879
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number17
DOIs
Publication statusPublished - 2013 Sep 6

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Raihan, M. J., Rajawinslin, R. R., Kavala, V., Kuo, C. W., Kuo, T. S., He, C. H., Huang, H. N., & Yao, C. F. (2013). Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides. Journal of Organic Chemistry, 78(17), 8872-8879. https://doi.org/10.1021/jo401283x