Iodine(III)-Mediated\nKeto-oximation of <i>O</i>‑Alkynyl Hydroxylamines:\nA Route to 3‑Acyl Isoxazolines\nand 1,2-Oxazines

An intramolecular iodine(III)-mediated\nketo-oximation\nof <i>O</i>-alkynyl hydroxylamines offers rapid and straightforward\naccess to 3-acyl Δ<sup>2</sup>-isoxazolines and 1,2-oxazines.\nThis approach features mild, metal-free, and aerobic reaction conditions\nwith good functional group tolerance. Moreover, the synthetic utility\nof this method is demonstrated by the synthesis of unique structural\nmotifs such as isoxazolidine, 3-vinyl isoxazoline, and 2,5-diphenylpyrazine\nderivatives by the conversion of 3-acyl Δ<sup>2</sup>-isoxazolines,\nthereby showcasing its efficiency and applicability in synthetic chemistry.

Publication Details

Journal
Figshare
Published
2024-11-04
DOI
https://doi.org/10.1021/acs.orglett.4c03835.s001
Primary Topic
Wheat and Barley Genetics and Pathology
Type
article
Field-Weighted Citation Impact
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article

Iodine(III)-Mediated\nKeto-oximation of O‑Alkynyl Hydroxylamines:\nA Route to 3‑Acyl Isoxazolines\nand 1,2-Oxazines

Figshare
Wheat and Barley Genetics and Pathology
article

Iodine(III)-Mediated\nKeto-oximation of O‑Alkynyl Hydroxylamines:\nA Route to 3‑Acyl Isoxazolines\nand 1,2-Oxazines

article en

Abstract

An intramolecular iodine(III)-mediated\nketo-oximation\nof <i>O</i>-alkynyl hydroxylamines offers rapid and straightforward\naccess to 3-acyl Δ<sup>2</sup>-isoxazolines and 1,2-oxazines.\nThis approach features mild, metal-free, and aerobic reaction conditions\nwith good functional group tolerance. Moreover, the synthetic utility\nof this method is demonstrated by the synthesis of unique structural\nmotifs such as isoxazolidine, 3-vinyl isoxazoline, and 2,5-diphenylpyrazine\nderivatives by the conversion of 3-acyl Δ<sup>2</sup>-isoxazolines,\nthereby showcasing its efficiency and applicability in synthetic chemistry.

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Openalex Percentile: Top 38%
Wheat and Barley Genetics and Pathology
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Iodine(III)-Mediated\nKeto-oximation of <i>O</i>‑Alkynyl Hydroxylamines:\nA Route to 3‑Acyl Isoxazolines\nand 1,2-Oxazines · Figshare (2024) | TGRS Research Map | TGRS