Journal of Organic Chemistry 2013-09-06

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

Index: J. Org. Chem. 78(17) , 8872-9, (2013)

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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.