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

被引：23

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

页码：6455 / 6460

页数：6

共 43 条

[1] Domino reactions of 1,3-bis-silyl enol ethers with benzopyrylium triflates:: Efficient synthesis of fluorescent 6H-benzo[c]chromen-6-ones, dibenzo[c,d]chromen-6-ones, and 2,3-dihydro-1H-4,6-dioxachrysen-5-ones [J].