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

Research output: Contribution to journalArticle

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 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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Oximes
Oxides
Halogenation
Bromosuccinimide
Ions
Derivatives
Hydrides
Oxidation
trichloroisocyanuric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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 journalArticle

Raihan, MJ, Rajawinslin, RR, Kavala, V, Kuo, CW, Kuo, TS, He, CH, Huang, HN & Yao, CF 2013, 'Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides', Journal of Organic Chemistry, vol. 78, no. 17, pp. 8872-8879. https://doi.org/10.1021/jo401283x
Raihan, Mustafa J. ; Rajawinslin, R. R. ; Kavala, Veerababurao ; Kuo, Chun Wei ; Kuo, Ting Shen ; He, Chiu Hui ; Huang, Hsiu Ni ; Yao, Ching Fa. / Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 17. pp. 8872-8879.
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AU - Kuo, Chun Wei

AU - Kuo, Ting Shen

AU - He, Chiu Hui

AU - Huang, Hsiu Ni

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