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

doi:10.1021/jo401283x

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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

11 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	8872-8879
頁數	8
期刊	Journal of Organic Chemistry
卷	78
發行號	17
DOIs	https://doi.org/10.1021/jo401283x
出版狀態	已發佈 - 2013 9月 6

ASJC Scopus subject areas

有機化學

存取文件

10.1021/jo401283x

其它文件與鏈接

CCDC 1422904: Experimental Crystal Structure Determination
Raihan, M. J. (Creator), Rajawinslin, R. R. (Creator), Kavala, V. (Creator), Kuo, C.-W. (Creator), Kuo, T.-S. (Creator), He, C.-H. (Creator), Huang, H.-N. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc1jrn42, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jrn42&sid=DataCite
資料集: Dataset

引用此

@article{64a40a2527ec40e09ac4f6563d2a7b6e,

title = "Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides",

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.",

author = "Raihan, \{Mustafa J.\} and Rajawinslin, \{R. R.\} and Veerababurao Kavala and Kuo, \{Chun Wei\} and Kuo, \{Ting Shen\} and He, \{Chiu Hui\} and Huang, \{Hsiu Ni\} and Yao, \{Ching Fa\}",

year = "2013",

month = sep,

day = "6",

doi = "10.1021/jo401283x",

language = "English",

volume = "78",

pages = "8872--8879",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

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 - https://www.scopus.com/pages/publications/84883817169

UR - https://www.scopus.com/pages/publications/84883817169#tab=citedBy

U2 - 10.1021/jo401283x

DO - 10.1021/jo401283x

M3 - Article

C2 - 23944682

AN - SCOPUS:84883817169

SN - 0022-3263

VL - 78

SP - 8872

EP - 8879

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N -oxides

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1422904: Experimental Crystal Structure Determination

引用此