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

doi:10.1021/jo401283x

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

Department of Chemistry

Research output: Contribution to journal › Article

9 Citations (Scopus)

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 language	English
Pages (from-to)	8872-8879
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	78
Issue number	17
DOIs	https://doi.org/10.1021/jo401283x
Publication status	Published - 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

Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides. / Raihan, Mustafa J.; Rajawinslin, R. R.; Kavala, Veerababurao; Kuo, Chun Wei; Kuo, Ting Shen; He, Chiu Hui; Huang, Hsiu Ni; Yao, Ching Fa.

In: Journal of Organic Chemistry, Vol. 78, No. 17, 06.09.2013, p. 8872-8879.

Research output: Contribution to journal › Article

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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.",

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10.1021/jo401283x