用于一锅法合成香豆素官能化吡咯并[2,1-]异喹啉的碱介导级联内酯化/1,3-偶极环加成途径
Base-Mediated Cascade Lactonization/1,3-Dipolar Cycloaddition Pathway for the One-Pot Assembly of Coumarin-Functionalized Pyrrolo[2,1-]isoquinolines.
作者信息
Tang Qiang, Liu Yanan, Fei BinBin, Tao Qianqian, Wang Chen, Jiang Xiaochun, He Xinwei, Shang Yongjia
机构信息
The Translational Research Institute for Neurological Disorders & Interdisciplinary Research Center of Neuromedicine and Chemical Biology of Wannan Medical College and Anhui Normal University, Department of Neurosurgery, The First Affiliated Hospital of Wannan Medical College (Yijishan Hospital of Wannan Medical College), Wuhu 241001, P. R. China.
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
出版信息
J Org Chem. 2024 Jun 21;89(12):8420-8434. doi: 10.1021/acs.joc.4c00239. Epub 2024 Jun 5.
An elegant and highly concise strategy for the construction of coumarin-functionalized pyrrolo[2,1-]isoquinolines from available propargylamines and isoquinolinium -ylides has been disclosed. In this reaction, isoquinolinium -ylides acted as a C2 synthon to form a coumarin ring as well as a 1,3-dipole to construct a pyrrole ring in a single pot. This cascade process involves 1,4-conjugate addition/lactonization/1,3-dipolar cycloaddition to construct four chemical bonds (one C-O bond and three C-C bonds) and two new heterocyclic skeletons. Additionally, most of these compounds showed good fluorescence properties and exhibited high molar extinction coefficient and large Stokes shifts.
已公开了一种从可用的炔丙胺和异喹啉叶立德构建香豆素官能化吡咯并[2,1 -]异喹啉的优雅且高度简洁的策略。在该反应中，异喹啉叶立德充当C2合成子以形成香豆素环，并作为1,3 -偶极子在一锅反应中构建吡咯环。这种串联过程涉及1,4 -共轭加成/内酯化/1,3 -偶极环加成，以构建四个化学键（一个C - O键和三个C - C键）和两个新的杂环骨架。此外，这些化合物中的大多数表现出良好的荧光性质，并具有高摩尔消光系数和大斯托克斯位移。
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