Efficient Synthesis of Functionalized Benzo[b][1,8]naphthyridine Derivatives via Three-Component Reaction Catalyzed by L-Proline

被引：40

作者：

Fu, Lei ^{[1
]}

Lin, Wei ^{[1
]}

Hu, Ming-Hua ^{[1
]}

Liu, Xue-Cheng ^{[1
]}

Huang, Zhi-Bin ^{[1
]}

Shi, Da-Qing ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

ACS COMBINATORIAL SCIENCE | 2014年 / 16卷 / 05期

关键词：

benzo[b][1,8]naphthyridine; three-component reaction; L-proline; ONE-POT SYNTHESIS; ASYMMETRIC MANNICH REACTIONS; HETEROCYCLIC KETENE AMINALS; MULTICOMPONENT REACTIONS; BIGINELLI REACTION; CONSTRUCTION; AGENTS; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; DOMINO; ACIDS;

D O I：

10.1021/co4001524

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A facile and efficient one-pot procedure for the preparation of functionalized benzo[b][1,8]naphthyridine derivatives by three-component reaction of 2-chloroquinoline-3-carbaldehyde, 1,3-dicarbonyl compounds, and enaminones catalyzed by L-proline is described. This new protocol has the advantages of environmental friendliness, good yields, and convenient operation.

引用

页码：238 / 243

页数：6

共 55 条

[51] Modulating the Reactivity of Heterocyclic Ketene Animals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-ιj][1,8]naphthyridines [J].

Wen, Li-Rong ;

Liu, Chao ;

Li, Ming ;

Wang, Li-Juan .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) :7605-7614

[52] A novel L-proline catalyzed Biginelli reaction:: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions [J].

Yadav, JS ;

Kumar, SP ;

Kondaji, G ;

Rao, RS ;

Nagaiah, K .

CHEMISTRY LETTERS, 2004, 33 (09) :1168-1169

[53] Microwave assisted synthesis of indolo[2,3-b]dibenzo[b,g] [1,8]naphthyridines [J].

Yamuna, Ezhumalai ;

Zeller, Matthias ;

Prasad, Karnam Jayarampillai Rajendra .

TETRAHEDRON LETTERS, 2012, 53 (12) :1514-1517

[54] Regioselective construction of 1,3-diazaheterocycle fused [1,2-a][1,8]naphthyridine derivatives via cascade reaction of quinolines with heterocyclic ketene aminals: a joint experimental-computational approach [J].

Zhang, Yi-Chuan ;

Liu, Zhi-Cheng ;

Yang, Sheng-Jiao ;

Zhang, Ji-Hong ;

Yan, Sheng-Jiao ;

Lin, Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (42) :7276-7288

[55] Clarification of the role of water in proline-mediated aldol reactions [J].

Zotova, Natalia ;

Franzke, Axel ;

Armstrong, Alan ;

Blackmond, Donna G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15100-+

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