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 lithiumaluminum hydride to synthesize an unprecedented type of Baylis-Hillman oxime, which underwent N-O coupling to produce new isoxazoline N-oxide derivative.
Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei116, Taiwan, R.O.C.
Mustafa J
MJ
Raihan
R R
RR
Rajawinslin
Veerababurao
V
Kavala
Chun-Wei
CW
Kuo
Ting-Shen
TS
Kuo
Chiu-Hui
CH
He
Hsiu-Ni
HN
Huang
Ching-Fa
CF
Yao
D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006219:Halogens / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry
D001577:Benzophenones; D006219:Halogens; D007477:Ions; D007555:Isoxazoles; D010087:Oxides; D010091:Oximes