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
Rok vydání:	2021
Předmět:	Reaction conditions Organic Chemistry Aromatization Biochemistry Combinatorial chemistry Tautomer Fluorescence chemistry.chemical_compound chemistry Cascade Functional group Physical and Theoretical Chemistry Oxoglutarate dehydrogenase complex Isomerization
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9c7130cf81c13e83823ac73df24e90d4 https://doi.org/10.1021/acs.orglett.1c02266 Zobrazit plný text záznamu