BF3<middle dot>OEt2 Catalyzed Cascade [4+2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives

被引：5

作者：

Wang, Yafei ^{[1
,2
]}

Wang, Yujia ^{[1
,2
]}

Qu, Jiaxin ^{[1
,2
]}

Yang, Tongtong ^{[1
,2
]}

Zhang, Yining ^{[1
,2
]}

Yuan, Chunhao ^{[3
]}

Guo, Hongchao ^{[4
]}

Wang, Chang ^{[1
,2
]}

机构：

[1] Shandong First Med Univ & Shandong Acad Med Sci, Sch Pharmaceut Sci, Med Sci & Technol Innovat Ctr, Jinan 250117, Shandong, Peoples R China

[2] Shandong First Med Univ & Shandong Acad Med Sci, Inst Mat Med, Med Sci & Technol Innovat Ctr, Jinan 250117, Shandong, Peoples R China

[3] Shandong First Med Univ & Shandong Acad Med Sci, Sch Chem & Pharmaceut Engn, Tai An 271016, Shandong, Peoples R China

[4] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 13期

基金：

中国国家自然科学基金;

关键词：

STEREOCONTROLLED SYNTHESIS; VINYL EPOXIDES; ACCESS; REARRANGEMENT; COUPLINGS; ALCOHOLS;

D O I：

10.1021/acs.joc.4c00742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A BF3<middle dot>OEt2-catalyzed cascade cyclization reaction of vinyloxirane with coumarin is described, affording the benzocoumarin derivatives with moderate to excellent yields (72-92%). The reaction demonstrates exceptional substrate tolerance and has been extensively explored for its potential in drug development, including scale-up experiments, functional group transformations, and screening of the products for anticancer activity. Moreover, the reaction mechanism has been rigorously validated through intermediate trapping and control experiments. Additionally, this reaction represents the uncommon nonmetal catalyzed intermolecular cyclization of vinyloxiranes.

引用

页码：9462 / 9472

页数：11

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