Iodine(III)-Mediated Keto-oximation of <i>O</i>-Alkynyl Hydroxylamines: A Route to 3-Acyl Isoxazolines and 1,2-Oxazines
An intramolecular iodine(III)-mediated keto-oximation of <i>O</i>-alkynyl hydroxylamines offers rapid and straightforward access to 3-acyl Δ<sup>2</sup>-isoxazolines and 1,2-oxazines. This approach features mild, metal-free, and aerobic reaction conditions with good functional group tolerance. Moreover, the synthetic utility of this method is demonstrated by the synthesis of unique structural motifs such as isoxazolidine, 3-vinyl isoxazoline, and 2,5-diphenylpyrazine derivatives by the conversion of 3-acyl Δ<sup>2</sup>-isoxazolines, thereby showcasing its efficiency and applicability in synthetic chemistry.
Authors
- Juhi Pal (ORCID: https://orcid.org/0000-0001-8552-1160)
- Kaushik C. Pansuriya (ORCID: https://orcid.org/0000-0002-8202-5791)
- Santosh J. Gharpure (ORCID: https://orcid.org/0000-0002-6653-7236)
- Showkat A. Hajam
- Sanyog Kumari (ORCID: https://orcid.org/0000-0002-8367-403X)
Institutions
- Indian Institute of Technology Bombay (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-04
- DOI
- https://doi.org/10.1021/acs.orglett.4c03835
- Citations
- 11
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.75
Funders
- Council of Scientific and Industrial Research, India
- Indian Institute of Technology Bombay
- Science and Engineering Research Board