Convenient One-Pot Three-Component Synthesis of Trifluoromethylated Tetrahydrobenzo[g]chromene Derivatives

被引：12

作者：

Duan, Yijun ^{[1
]}

Wang, Xu ^{[1
]}

Xu, Xiaoling ^{[1
]}

Kang, Zhangping ^{[1
]}

Zhang, Min ^{[1
]}

Song, Liping ^{[1
,2
]}

Deng, Hongmei ^{[3
]}

机构：

[1] Shanghai Univ, Sch Sci, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[3] Shanghai Univ, Lab Microstruct, Shanghai 200444, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 15期

基金：

中国国家自然科学基金;

关键词：

multicomponent reactions; quinones; aldehydes; cyclizations; heterocycles; catalysis; fluorine; fused-ring systems; EFFICIENT SYNTHESIS; ACIDS; PRODUCTS; KETONES; ESTERS; ANALOG; ROUTE;

D O I：

10.1055/s-0033-1338487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of ethyl 4-(het)aryl-5,10-dioxo-2-hydroxy-2-(trifluoromethyl)-3,4,5,10-tetrahydro-2H-benzo[g]chromene-3-carboxylates were efficiently synthesized from 2-hydroxynaphthoquinone, aromatic aldehydes, and ethyl 4,4,4-trifluoro-3-oxobutanoate by a one-pot multicomponent reaction catalyzed by the combination of ammonium acetate and acetic acid. The benzo-chromenes are presumably formed through an initial Knoevenagel condensation followed by a Michael addition and regioselective intramolecular annulation. The dehydration reaction of the hemiketal moiety to the corresponding dehydrated product was also studied.

引用

页码：2193 / 2200

页数：8

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