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

J Org Chem. 2011 Jan 21;76(2):424-34. doi: 10.1021/jo1018393. Epub 2010 Dec 22.

Authors

Mustafa J Raihan¹, Veerababurao Kavala, Pateliya Mujjamil Habib, Qiao-Zhi Guan, Chun-Wei Kuo, Ching-Fa Yao

Affiliation

¹ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, Taiwan 116, Republic of China.

PMID: 21175154
DOI: 10.1021/jo1018393

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography
Cyclic N-Oxides / chemical synthesis*
Cyclic N-Oxides / chemistry*
Iodobenzenes / chemistry*
Isoxazoles / chemical synthesis*
Isoxazoles / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Oxidative Coupling
Solvents / chemistry
Tosyl Compounds / chemistry*

Substances

(hydroxy(tosyloxy)iodo)benzene
Cyclic N-Oxides
Iodobenzenes
Isoxazoles
Solvents
Tosyl Compounds