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Synthesis 2023; 55(12): 1904-1914
DOI: 10.1055/s-0042-1752403
DOI: 10.1055/s-0042-1752403
paper
Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions
We sincerely thank Science and Engineering Research Board (SERB, research grant No. EMR/2017/000174), New Delhi for financial support to this work. The authors thank DST-FIST, New Delhi for providing funding (SR/FST/CS-II/2018/72 (C)) to the department for 500 MHz facility. R.B. thanks University Grants Commission (UGC) and M.R. thanks Ministry of Education India (MoE) for research fellowships.
Abstract
A metal- and base-free, robust, and convenient approach for the synthesis of isoxazoline derivatives is reported. This protocol involves 1,3-dipolar cycloaddition between in situ generated nitrile oxides from the corresponding aldoximes using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) and maleimides, styrene and acrylonitrile. The described methodology is very attractive as it is operationally simple, has broad scope, and does not require any base, metal, or other additives.
Key words
arylaldoximes - C–C and C–O bond formation - fused isoxazolines - heterocycles - hypervalent iodine - nitrile oxides - oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1752403.
- Supporting Information
- CIF File
Publication History
Received: 23 November 2022
Accepted after revision: 12 January 2023
Article published online:
01 March 2023
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