Copper-Catalyzed Synthesis of Furo[3,2-c]coumarins and Dihydrofuro[3,2-c]coumarins through a Propargylation/Alkyne Oxacyclization/Isomerization Cascade under Microwave Irradiation

被引：20

作者：

Zhang, Xiao-Yan ^{[1
,2
]}

Hu, Li-Li ^{[2
]}

Shen, Ze ^{[2
]}

Chen, Zhong-Zhu ^{[2
]}

Xu, Zhi-Gang ^{[2
]}

Li, Shi-Qiang ^{[2
]}

Xie, Jian-Wu ^{[1
]}

Cui, Hai-Lei ^{[2
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem & Life Sci, Key Lab, Minist Educ Adv Catalysis Mat, Jinhua 321004, Peoples R China

[2] Chongqing Univ Arts & Sci, Int Acad Targeted Therapeut & Innovat, Chongqing 402160, Peoples R China

来源：

SYNLETT | 2015年 / 26卷 / 20期

基金：

美国国家科学基金会;

关键词：

cascade reactions; coumarins; propargyl acetates; furocoumarins; cyclization; SECONDARY PROPARGYLIC ALCOHOLS; ASSISTED ORGANIC-SYNTHESIS; ONE-POT SYNTHESIS; TETRASUBSTITUTED FURANS; BREAST-CANCER; 1,3-DICARBONYL DERIVATIVES; BIOLOGICAL EVALUATION; SUBSTITUTED FURANS; NEO-TANSHINLACTONE; ANTITUMOR AGENTS;

D O I：

10.1055/s-0035-1560500

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel copper-catalyzed microwave-promoted propargylation/alkyne oxacyclization/isomerization cascade for the synthesis of 2-methylfuro[3,2-c]coumarins has been developed. This reaction provides furo[3,2-c]coumarins in moderate to good yields (82%) from readily available 4-hydroxycoumarins and terminal propargyl acetates as starting materials. Interestingly, by changing the solvent from dimethyl sulfoxide to 1,2-dichloroethane, the isomeric series of 2-methylene-2,3-dihydrofuro[3,2-c]coumarins were obtained in good to acceptable yields (85%).

引用

页码：2821 / 2825

页数：5

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