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  • 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.

The Journal of organic chemistry (2013-08-16)
Mustafa J Raihan, R R Rajawinslin, Veerababurao Kavala, Chun-Wei Kuo, Ting-Shen Kuo, Chiu-Hui He, Hsiu-Ni Huang, Ching-Fa Yao
PMID23944682
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.