Lactonization of 2-Alkynylbenzoates for the Assembly of lsochromenones Mediated by BF3•Et2O

被引：22

作者：

Zhang, Xiang ^{[1
]}

Wan, Xintong ^{[1
]}

Cong, Ying ^{[1
]}

Zhen, Xiaohua ^{[1
]}

Li, Qiao ^{[1
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
,2
]}

Zhao, Kang ^{[1
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 16期

基金：

中国国家自然科学基金;

关键词：

HYDRANGEAE-DULCIS FOLIUM; CATALYZED CYCLIZATION; CASCADE ANNULATIONS; BIOACTIVE FUNCTIONS; THUNBERGINOL-B; ISOCOUMARINS; ACIDS; ALKYNES; PHTHALIDES; HETEROCYCLES;

D O I：

10.1021/acs.joc.9b01601

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3 center dot Et2O-mediated 6-endo-dig cyclization process under mild conditions. An alternative mechanistic pathway in which BF3 center dot Et2O activates the carbonyl of the ester moiety, rather than the alkyne triple bond, was postulated on the basis of control experiment results. Gram-scale reaction and further application for the assembly of more complex molecules demonstrated the practicability of the protocol.

引用

页码：10402 / 10411

页数：10

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