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 241000, P.R. China.
State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, P.R. China.
Org Lett. 2021 Aug 20;23(16):6455-6460. doi: 10.1021/acs.orglett.1c02266. Epub 2021 Aug 3.
A DBU-mediated cascade strategy of propargylamines with dimethyl 3-oxoglutarate for constructing a functionalized benzo[]chromen-6-one core has been achieved. This cascade process presumably involves a sequence of 1,4-conjugate addition, followed by lactonization, alkyne-allene isomerization, enol-keto tautomerization, 6π-electrocyclization, and aromatization. This protocol features mild reaction conditions, simple operation, rich structural diversity, and good functional group tolerance. A photophysical survey reveals that the benzo[]chromen-6-one products exhibit fluorescence properties and show potential for exploring fluorescent material applications.
一种通过 DBU 介导的丙炔胺与二甲基 3-氧代戊二酸的级联策略已被用于构建具有官能化苯并[ ]色烯-6-酮核心的结构。该级联过程可能涉及 1,4-共轭加成、内酯化、炔丙基-丙二烯异构化、烯醇-酮互变异构、6π-电环化和芳构化等一系列反应。该方法具有反应条件温和、操作简单、结构多样性丰富和官能团容忍度好等特点。光物理研究表明，苯并[ ]色烯-6-酮产物具有荧光性质，有望用于探索荧光材料的应用。
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