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

共 62 条

[31] Calothrixins, a New Class of Human DNA Topoisomerase I Poisons [J].

Khan, Qasim A. ;

Lu, Jun ;

Hecht, Sidney M. .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (03) :438-442

[32] Isolation and synthesis of biologically active carbazole alkaloids [J].

Knölker, HJ ;

Reddy, KR .

CHEMICAL REVIEWS, 2002, 102 (11) :4303-4427

[33]

Lamberk R.W., 1997, Patent, Patent No. [WO9,706,178, 9706178]

[34] The "Off-Shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinone [J].

Leroux, Frederic ;

Lefebvre, Olivier ;

Schlosser, Manfred .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) :3147-3151

[35] Simple synthesis of 6-(trifluoromethyl)-2,4,5,6-tetrahydropyrazolo[3,4-b]pyran derivatives by one-pot, three-component reactions [J].

Li, Dong-Mei ;

Song, Li-Ping ;

Li, Xian-Fu ;

Xing, Chun-Hui ;

Peng, Wei-Min ;

Zhu, Shi-Zheng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3520-3525

[36] Regioselective synthesis of 6-trifluoromethyl-1,4,5,6-tetrahydropyrazolo[3,4-b]pyran derivatives [J].

Li, Dongmei ;

Song, Liping ;

Song, Shaodi ;

Zhub, Shizheng .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (08) :952-957

[37] Study on the reactions of ethyl 4,4,4-trifluoro-3-oxobutanoate with arylidenemalononitriles [J].

Li, XF ;

Song, LP ;

Xin, CH ;

Zhao, JW ;

Zhu, SZ .

TETRAHEDRON, 2006, 62 (10) :2255-2263

[38] Design of antineoplastic agents on the basis of the ''2-phenylnaphthalene-type'' structural pattern .3. Synthesis and biological activity evaluation of 5H-benzo[b]naphtho[2,3-d]pyrrole-6,11-dione derivatives [J].

Luo, YL ;

Chou, TC ;

Cheng, CC .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (01) :113-117

[39] Alternative esters in the synthesis of ZD0947 [J].

Moseley, JD .

TETRAHEDRON LETTERS, 2005, 46 (18) :3179-3181

[40] Concise synthesis of guanidine-containing heterocycles using the Biginelli reaction [J].

Nilsson, Bradley L. ;

Overman, Larry E. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7706-7714

← 1 2 3 4 5 6 7 →