Synthesis of isoxazoline N -oxides via [hydroxy(tosyloxy)iodo]benzene (HTIB)-mediated oxidative N-O coupling

Mustafa J. Raihan; Veerababurao Kavala; Pateliya Mujjamil Habib; Qiao Zhi Guan; Chun Wei Kuo; Ching Fa Yao

doi:10.1021/jo1018393

Synthesis of isoxazoline N -oxides via [hydroxy(tosyloxy)iodo]benzene (HTIB)-mediated oxidative N-O coupling

Mustafa J. Raihan, Veerababurao Kavala, Pateliya Mujjamil Habib, Qiao Zhi Guan, Chun Wei Kuo, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

An HTIB mediated oxidative N-O coupling strategy for the synthesis of some isoxazoline N-oxide derivatives from β-hydroxyketoximes is described, along with a comparative study of the efficiency of N-O coupling in two different solvents. A plausible mechanism for the conversion is proposed.

Original language	English
Pages (from-to)	424-434
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	76
Issue number	2
DOIs	https://doi.org/10.1021/jo1018393
Publication status	Published - 2011 Jan 21

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo1018393

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title = "Synthesis of isoxazoline N -oxides via [hydroxy(tosyloxy)iodo]benzene (HTIB)-mediated oxidative N-O coupling",

abstract = "An HTIB mediated oxidative N-O coupling strategy for the synthesis of some isoxazoline N-oxide derivatives from β-hydroxyketoximes is described, along with a comparative study of the efficiency of N-O coupling in two different solvents. A plausible mechanism for the conversion is proposed.",

author = "Raihan, {Mustafa J.} and Veerababurao Kavala and Habib, {Pateliya Mujjamil} and Guan, {Qiao Zhi} and Kuo, {Chun Wei} and Yao, {Ching Fa}",

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volume = "76",

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journal = "Journal of Organic Chemistry",

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AU - Raihan, Mustafa J.

AU - Kavala, Veerababurao

AU - Habib, Pateliya Mujjamil

AU - Guan, Qiao Zhi

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2011/1/21

Y1 - 2011/1/21

N2 - An HTIB mediated oxidative N-O coupling strategy for the synthesis of some isoxazoline N-oxide derivatives from β-hydroxyketoximes is described, along with a comparative study of the efficiency of N-O coupling in two different solvents. A plausible mechanism for the conversion is proposed.

AB - An HTIB mediated oxidative N-O coupling strategy for the synthesis of some isoxazoline N-oxide derivatives from β-hydroxyketoximes is described, along with a comparative study of the efficiency of N-O coupling in two different solvents. A plausible mechanism for the conversion is proposed.

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M3 - Article

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AN - SCOPUS:78651512791

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ER -

Synthesis of isoxazoline N -oxides via [hydroxy(tosyloxy)iodo]benzene (HTIB)-mediated oxidative N-O coupling

Abstract

ASJC Scopus subject areas

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CCDC 792922: Experimental Crystal Structure Determination

CCDC 792920: Experimental Crystal Structure Determination

CCDC 792919: Experimental Crystal Structure Determination

Cite this

Synthesis of isoxazoline N -oxides via [hydroxy(tosyloxy)iodo]benzene (HTIB)-mediated oxidative N-O coupling

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 792922: Experimental Crystal Structure Determination

CCDC 792920: Experimental Crystal Structure Determination

CCDC 792919: Experimental Crystal Structure Determination

Cite this