Park Eunhui, Tambe Shrikant D, Lee Jongbok, Cho Eun Jin
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974, Republic of Korea.
Department of Biological & Chemical Engineering, Hongik University, 2639 Sejong-ro, Jochiwon-eup, Sejong, 30016, Republic of Korea.
ChemSusChem. 2025 Feb 16;18(4):e202402004. doi: 10.1002/cssc.202402004. Epub 2024 Nov 8.
We report a photosynthetic method for producing 2H-benzo[b][1,4]oxazin-2-ones from aryl azides and α-ketoacids. This method is highly sustainable, requiring only visible light irradiation of the substrates and no external additives. Furthermore, we implemented a continuous-flow system to achieve efficient light irradiation and rapid mixing, significantly improving reaction efficiency and reducing reaction time compared to the batch process. The flow system enabled gram-scale synthesis. We also demonstrated the utility of the products, by employing the benzo[1,4]oxazin-2-one moiety as a directing group for C-H activation on the 3-aryl substituent. This green approach highlights the potential for developing environmentally friendly synthetic processes.
我们报道了一种从芳基叠氮化物和α-酮酸制备2H-苯并[b][1,4]恶嗪-2-酮的光合方法。该方法具有高度可持续性，仅需对底物进行可见光照射，无需外部添加剂。此外，我们采用了连续流动系统以实现高效的光照射和快速混合，与间歇式工艺相比，显著提高了反应效率并缩短了反应时间。该流动系统实现了克级规模的合成。我们还通过将苯并[1,4]恶嗪-2-酮部分用作3-芳基取代基上C-H活化的导向基团，展示了产物的实用性。这种绿色方法凸显了开发环境友好型合成工艺的潜力。
