Synthesis of Isoquinoline N-Oxides via Hypervalent Iodine-Mediated Oxidative Cyclization of Ketoximes with Alkenes
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Reported herein is the development of an intramolecular oxidative cyclization of ketoximes with alkenes for the preparation of isoquinoline N -oxides. The reaction, which utilizes phenyliodine bis(trifluoroacetate) (PIFA) as an oxidant and 2,2,2-trifluoroethanol (TFE) as a solvent, proceeds to afford various N -heterocyclic products, including aryl/heteroaryl-fused pyridine N -oxides, isoindole N -oxides, and 2-benzazepine derivatives. Preliminary experimental and computational mechanistic studies suggest that the ionic pathway is the primary mechanism. The synthetic utility of the developed method was highlighted via several product transformations.
Source: The Journal of Organic Chemistry
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Funders: Thailand Toray Science Foundation, Chulabhorn Royal Academy, National Research Council of Thailand, Chulabhorn Research Institute, Chiba University, Ministry of Higher Education, Science, Research and Innovation, Thailand, Thailand Science Research and Innovation, Toray Science Foundation, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Japan Society for the Promotion of Science
OpenAlex ID: W4411050883