Photoisomerization of Isatogens to Benzoxazin-4-ones
Abstract
A mild photoinduced isomerization of isatogens to benzoxazin-4-ones is described. Upon irradiation at 370 nm, a broad range of 2-aryl- and 2-alkyl-substituted isatogens undergo efficient scaffold reorganization under catalyst-free conditions to afford benzoxazin-4-ones in good to excellent yields. The transformation tolerates diverse substitution patterns, including heteroaryl and strained alkyl groups, and is readily scalable. Mechanistic experiments support participation of an excited-state pathway, and inclusion of catalytic 2-picolinic acid provided reproducible outcomes. For a nitro-substituted substrate, a distinct reaction pathway is observed, leading to the formation of a toluene-derived adduct. These results establish isatogens as versatile photochemical precursors to benzoxazinone scaffolds under operationally simple conditions.
Fields of Study & Subjects
Radical Photochemical Reactions
Photochromic and Fluorescence Chemistry
Quinazolinone synthesis and applications
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 19
- Pages
- 6768–6782
- Publication date
- 5 May 2026
- Language
- EN