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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 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 Sept 6

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo401283x

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@article{64a40a2527ec40e09ac4f6563d2a7b6e,

title = "Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides",

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}",

year = "2013",

month = sep,

day = "6",

doi = "10.1021/jo401283x",

language = "English",

volume = "78",

pages = "8872--8879",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides

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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U2 - 10.1021/jo401283x

DO - 10.1021/jo401283x

M3 - Article

C2 - 23944682

AN - SCOPUS:84883817169

SN - 0022-3263

VL - 78

SP - 8872

EP - 8879

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

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

Abstract

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CCDC 1422904: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1422904: Experimental Crystal Structure Determination

Cite this