School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, an OCC of Homi Bhabha National Institute, Khurda - 752050, Odisha, India.
J Org Chem. 2023 Jul 7;88(13):8843-8853. doi: 10.1021/acs.joc.3c00645. Epub 2023 Jun 20.
In the presence of Cu(OTf) (5 mol %) and KOBu, a synergistic effect of the -arylation process on 2-amino-3-arylquinolines is observed. Within 4 h, this method provides a wide variety of norneocryptolepine analogues with good to excellent yields. Overall, a double heteroannulation strategy for the synthesis of indoloquinoline alkaloids from nonheterocyclic precursors is demonstrated. Mechanistic investigations establish that the reaction proceeds via the SAr pathway. Despite moderate yields, the one-pot, two-step double heteroannulation illustrates that this procedure is highly atom-efficient. Neocryptolepine, a natural product, is also synthesized from indoloquinoline. A brief study of the photophysical properties of selected norneocryptolepine analogues is also discussed.
在 Cu(OTf)（5 mol %）和 KOBu 的存在下，观察到 2-氨基-3-芳基喹啉的 -芳基化过程的协同效应。在 4 小时内，该方法提供了广泛的具有良好至优异收率的诺内奥克罗普林类似物。总体而言，展示了一种从非杂环前体合成吲哚喹啉生物碱的双杂环化策略。机理研究表明，反应通过 SAr 途径进行。尽管产率中等，但一锅两步双杂环化说明了该方法具有很高的原子经济性。天然产物新克罗普林也可由吲哚喹啉合成。还讨论了选定的诺内奥克罗普林类似物的光物理性质的简要研究。
