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 › peer-review

10 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

ASJC Scopus subject areas

Organic Chemistry

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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 › peer-review

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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.",

author = "Raihan, {Mustafa J.} and Rajawinslin, {R. R.} and Veerababurao Kavala and Kuo, {Chun Wei} and Kuo, {Ting Shen} and He, {Chiu Hui} and Huang, {Hsiu Ni} and Yao, {Ching Fa}",

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AU - Raihan, Mustafa J.

AU - Rajawinslin, R. R.

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Kuo, Ting Shen

AU - He, Chiu Hui

AU - Huang, Hsiu Ni

AU - Yao, Ching Fa

PY - 2013/9/6

Y1 - 2013/9/6

N2 - 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.

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

Abstract

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