BF<sub>3</sub>-Mediated C2-Amidation of Quinoline <i>N-</i>Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-<i>N-</i>(Trifluoroethyl)amidoquinolines
A Lewis acid-mediated C2-<i>N-</i>trifluoroethylamidation of quinolines, employing quinoline <i>N-</i>oxides, trifluorodiazoethane, and acetonitrile to forge a new class of <i>N-</i>(quinolin<i>-</i>2-yl)-<i>N-</i>(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-<i>N-</i>(trifluoroethyl)acetamide derivatives in high yields.
Authors
- Kishor Mohanan (ORCID: https://orcid.org/0000-0001-5602-7112)
- Anamika Dhami (ORCID: https://orcid.org/0000-0002-2529-1356)
- Sanoop P. Chandrasekharan
Institutions
- Central Drug Research Institute (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.orglett.4c04127
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.21
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- University Grants Committee
- Science and Engineering Research Board