ArticleThe Journal of organic chemistry2026
Photoisomerization of Isatogens to Benzoxazin-4-ones.
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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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.
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