Sharjah Institute for Medical Research, University of Sharjah, P.O. Box 27272, Sharjah27272, UAE.
Department of Biology, Chemistry and Environmental Sciences, American University of Sharjah, P.O. Box 26666, Sharjah26666, UAE.
J Org Chem. 2022 Dec 16;87(24):16722-16735. doi: 10.1021/acs.joc.2c02380. Epub 2022 Dec 1.
A one-pot, metal-free, light-driven [4+2]-cycloaddition reaction is described by accessing a diverse collection of chromeno[4,3-]quinoline and chromeno[4,3-][1,8]naphthyridine scaffolds in a diastereoselective manner. This process delivered stereoisomers, which were challenging to produce by an inverse-demand Diels-Alder reaction. The tetracyclic products were provided in good yields, promoted by rose bengal and blue light in a single operation. The developed protocol proceeded efficiently without the need for expensive photosensitizers such as Ir or Ru complexes. The cascade is modular and step-economic, and the substrate scope is wide. Polycyclic architectures can be assembled from readily available aniline, aminoazine, indole, and salicylaldehyde derivatives.
本文描述了一种一锅、无金属、光驱动的[4+2]-环加成反应，通过以非对映选择性方式获得了多种色烯并[4,3-]喹啉和色烯并[4,3-][1,8]萘啶骨架。该过程提供了立体异构体，这是通过逆需求 Diels-Alder 反应难以产生的。在单一操作中，四元环产物在 Rose Bengal 和蓝光的促进下以良好的收率得到。该方法高效进行，无需使用昂贵的光敏剂，如 Ir 或 Ru 配合物。该级联反应具有模块化和经济性，底物范围广泛。多环架构可以从易于获得的苯胺、氨基嗪、吲哚和水杨醛衍生物中组装得到。
