Work

Photoinduced Cascade Reaction of Ene‐Yne‐Oxazoles with Trimethylsilyl Azide and N‐Iodosuccinamide: Synthesis of Azidyl Spiroindenoxazolones

Year: 2025

Type: article

Abstract: An intriguing photoinduced azidation cyclization of ene‐yne‐oxazolones using trimethylsilyl azide (TMSN3) 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‐N3 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.

Source: Chemistry - An Asian Journal

DOI: 10.1002/asia.202500332

Authors: Sireethon Khotsombat, Rattana Worayuthakarn, Kittipong Chainok, Somsak Ruchirawat, Nopporn Thasana

Institutions: Chulabhorn Graduate Institute, Chulabhorn Research Institute, Thammasat University, Ministry of Higher Education, Science, Research and Innovation

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze