Cascade Lactonization/Benzannulation of Propargylamines with Dimethyl 3-Oxoglutarate for Modular Assembly of Hydroxylated/Arene-Functionalized Benzo[c]chromen-6-ones

被引：22
作者：
Duan, Jiahui [1 ]
He, Xinwei [1 ]
Choy, Pui Ying [2 ]
Wang, Qi [1 ]
Xie, Mengqing [1 ]
Li, Ruxue [1 ]
Xu, Keke [1 ]
Shang, Yongjia [1 ]
Kwong, Fuk Yee [2 ,3 ]
机构：
[1] Anhui Normal Univ, Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat, Minist Educ,State Key Lab Cultivat Base,Coll Chem, Wuhu 241000, Peoples R China
[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Peoples R China
[3] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
TRANSITION-METAL-FREE; CATALYZED C(SP(2))-H; EFFICIENT SYNTHESIS; DOMINO REACTIONS; BIARYL LACTONES; ANNULATION; LACTONIZATION; EXTENSION; DIVERSE;
D O I：
10.1021/acs.orglett.1c02266
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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, 6p-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.
引用
收藏
页码：6455 / 6460
页数：6
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