Cascade Lactonization/Benzannulation of Propargylamines with Dimethyl 3-Oxoglutarate for Modular Assembly of Hydroxylated/Arene-Functionalized Benzo[c]chromen-6-ones
Autor: | Jiahui Duan, Xinwei He, Pui Ying Choy, Fuk Yee Kwong, Keke Xu, Mengqing Xie, Qi Wang, Yongjia Shang, Ruxue Li |
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Rok vydání: | 2021 |
Předmět: | |
Zdroj: | Organic Letters. 23:6455-6460 |
ISSN: | 1523-7052 1523-7060 |
Popis: | A DBU-mediated cascade strategy of propargylamines with dimethyl 3-oxoglutarate for constructing a functionalized benzo[c]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[c]chromen-6-one products exhibit fluorescence properties and show potential for exploring fluorescent material applications. |
Databáze: | OpenAIRE |
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