Halonium Ion Mediated Synthesis of 2‑Halomethylene-3-oxoketoxime Derivatives from Isoxazoline N‑Oxides

Halonium Ion Mediated Synthesis of 2‑Halomethylene-3-oxoketoxime Derivatives from Isoxazoline N‑Oxides

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 lithi...

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Veröffentlicht in:Journal of organic chemistry 2013-09, Vol.78 (17), p.8872-8879
Hauptverfasser: Raihan, Mustafa J, Rajawinslin, R. R, Kavala, Veerababurao, Kuo, Chun-Wei, Kuo, Ting-Shen, He, Chiu-Hui, Huang, Hsiu-Ni, Yao, Ching-Fa
Format: Artikel
Sprache:eng
Schlagworte:
Benzophenones - chemical synthesis
Benzophenones - chemistry
Crystallography, X-Ray
Halogens - chemistry
Ions - chemistry
Isoxazoles - chemistry
Models, Molecular
Molecular Structure
Oxides - chemistry
Oximes - chemical synthesis
Oximes - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401283x