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 language | English |
|---|---|
| Pages (from-to) | 8872-8879 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2013 Sep 6 |
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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 journal › Article
}
TY - JOUR
T1 - Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides
AU - Raihan, Mustafa J.
AU - Rajawinslin, R. R.
AU - Kavala, Veerababurao
AU - Kuo, Chun Wei
AU - Kuo, Ting Shen
AU - He, Chiu Hui
AU - Huang, Hsiu Ni
AU - Yao, Ching Fa
PY - 2013/9/6
Y1 - 2013/9/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84883817169&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84883817169&partnerID=8YFLogxK
U2 - 10.1021/jo401283x
DO - 10.1021/jo401283x
M3 - Article
C2 - 23944682
AN - SCOPUS:84883817169
VL - 78
SP - 8872
EP - 8879
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -