Photoinduced Cascade Reaction of Ene‐Yne‐Oxazoles with Trimethylsilyl Azide and <i>N</i>‐Iodosuccinamide: Synthesis of Azidyl Spiroindenoxazolones
An intriguing photoinduced azidation cyclization of ene-yne-oxazolones using trimethylsilyl azide (TMSN<sub>3</sub>) as an azide source and N-iodosuccinimide (NIS) as the iodine source provided access to the corresponding iodobenzylidene spiroindenoxazolones in good yields as a 1:1 mixture of diastereomers (d.r. ratio). A simple and mild metal-free condition was developed by using blue LEDs to induce the formation of the azidyl radical from TMS-N<sub>3</sub> as an azide source followed by its aza-1,4-addition and the ensuing 5-exo-dig cyclization to forge multiple bond formations of C─C, C─N, and C─I to furnish the desired spiroindenoxazolones.
Authors
- Kittipong Chainok (ORCID: https://orcid.org/0000-0003-1486-9164)
- Nopporn Thasana (ORCID: https://orcid.org/0000-0002-0572-4871)
- Somsak Ruchirawat
- Rattana Worayuthakarn
- Sireethon Khotsombat
Institutions
- Thammasat University (TH)
- Chulabhorn Graduate Institute (TH)
- Chulabhorn Research Institute (TH)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2025-04-14
- DOI
- https://doi.org/10.1002/asia.202500332
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Chulabhorn Royal Academy
- Thammasat University
- Chulabhorn Research Institute
- Thailand Science Research and Innovation
- Chulabhorn Graduate Institute, Chulabhorn Royal Academy