Cascade Reaction of Isatins with Heterocyclic Ketene Aminals: Synthesis of Imidazopyrroloquinoline Derivatives

被引：120

作者：

Yu, Fuchao ^{[1
]}

Yan, Shengjiao ^{[1
]}

Hu, Ling ^{[1
]}

Wang, Yongchao ^{[1
]}

Lin, Jun ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resources, Kunming 650091, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 18期

关键词：

ADENOSINE RECEPTOR ANTAGONISTS; IN-VITRO; ANTIPROLIFERATIVE EVALUATION; QUINOLINE SYNTHESIS; ANTIBACTERIAL; AGENTS; CONSTRUCTION; PYRIDINE; NITROGEN; TAS-103;

D O I：

10.1021/ol201783d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient route for the synthesis of highly substituted imidazopyrroloquinoline derivatives by simply refluxing a reaction mixture of different types of isatins and heterocyclic ketene aminals (HKAs) by acetic acid was developed. This method is suitable for combinatorial and parallel syntheses in drug discovery; consequently, a library of highly substituted imidazopyrroloquinoline derivatives was rapidly constructed using the present protocol.

引用

收藏

页码：4782 / 4785

页数：4

相关论文

共 57 条

[1] Synthesis of novel steroidal heterocyclic derivatives as antibacterial agents [J].

Abdelhalim, Mervat M. ;

El-Saidi, Manal M. T. ;

Rabie, Samira T. ;

Elmegeed, Gamal A. .

STEROIDS, 2007, 72 (05) :459-465

[2] Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach, a Recyclable and Water Tolerant-Acidic Catalyst for One-Pot Friedlander Quinoline Synthesis [J].

Akbari, Jafar ;

Heydari, Akbar ;

Kalhor, Hamid Reza ;

Kohan, Sirus Azizian .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :137-140

[3] In vitro antitumor activity of TAS-103, a novel quinoline derivative that targets topoisomerases I and II [J].

Aoyagi, Y ;

Kobunai, T ;

Utsugi, T ;

Oh-hara, T ;

Yamada, Y .

JAPANESE JOURNAL OF CANCER RESEARCH, 1999, 90 (05) :578-587

[4] New 2-arylpyrazolo[4,3-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Tabrizi, MA ;

Preti, D ;

Bovero, A ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :5001-5008

[5] SYNTHESIS AND REACTIONS OF 1,1-DIIODODINITROETHYLENE [J].

BAUM, K ;

BIGELOW, SS ;

NGUYEN, NV ;

ARCHIBALD, TG ;

GILARDI, R ;

FLIPPENANDERSON, JL ;

GEORGE, C .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :235-241

[6]

Borsche W, 1937, LIEBIGS ANN CHEM, V532, P146

[7] THE PFITZINGER REACTION IN THE SYNTHESIS OF QUINOLINE DERIVATIVES [J].

BUUHOI, NP ;

ROYER, R ;

XUONG, ND ;

JACQUIGNON, P .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (09) :1209-1224

[8] Pyrano[3,2-c]quinoline-6-Chlorotacrine Hybrids as a Novel Family of Acetylcholinesterase- and β-Amyloid-Directed Anti-Alzheimer Compounds [J].

Camps, Pelayo ;

Formosa, Xavier ;

Galdeano, Carles ;

Munoz-Torrero, Diego ;

Ramirez, Lorena ;

Gomez, Elena ;

Isambert, Nicolas ;

Lavilla, Rodolfo ;

Badia, Albert ;

Victoria Clos, M. ;

Bartolini, Manuela ;

Mancini, Francesca ;

Andrisano, Vincenza ;

Arce, Mariana P. ;

Isabel Rodriguez-Franco, M. ;

Huertas, Oscar ;

Dafni, Thomai ;

Javier Luque, F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (17) :5365-5379

[9] Synthesis and anticancer evaluation of certain indolo(2,3-b]quinoline derivatives [J].

Chen, YL ;

Hung, HM ;

Lu, CM ;

Li, KC ;

Tzeng, CC .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (24) :6539-6546

[10] Synthesis and anti-inflammatory evaluation of 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives.: Part 3 [J].

Chen, YL ;

Chen, IL ;

Lu, CM ;

Tzeng, CC ;

Tsao, LT ;

Wang, JP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (02) :387-392

← 1 2 3 4 5 6 →