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

被引：39

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

[1] Morita-Baylis-Hillman Route to 8,9,9a,10-Tetrahydrobenzo[b][1,8]naphthyridine-6(7H)-ones and 3,4,4a,5-Tetrahydrodibenzo[b,g][1,8]naphthyridine-1(2H)-ones [J].

Ahn, Sang-Hyun ;

Jang, Seung Soon ;

Kim, Yong Hyun ;

Lee, Kee-Jung .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (08) :3145-3148

[2] Proline-catalyzed diastereoselective direct aldol reaction between 4-oxoazetidine-2-carbaldehydes and ketones [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo ;

Torres, M. Rosario .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4818-4822

[3] QSAR analysis of 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridines with anticancer activity [J].

Atanasova, Mariyana ;

Ilieva, Sonia ;

Galabov, Boris .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (09) :1184-1192

[4] Pd-assisted multicomponent synthesis of heterocycles [J].

Balme, G ;

Bossharth, E ;

Monteiro, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111

[5] POTENTIAL ANTIMALARIALS .1. 1,8-NAPHTHYRIDINES [J].

BARLIN, GB ;

TAN, WL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (05) :1065-1073

[6] Mechanistic Variations of the Povarov Multicomponent Reaction and Related Processes [J].

Bello, Davide ;

Ramon, Rosario ;

Lavilla, Rodolfo .

CURRENT ORGANIC CHEMISTRY, 2010, 14 (04) :332-356

[7] Synthesis of 7-aryl-1,8-naphthyridines via addition of aryl boronic acids to 1,8-naphthyridine N-oxides [J].

Bennie, Linsey S. ;

Burton, Paul M. ;

Morris, James A. .

TETRAHEDRON LETTERS, 2011, 52 (37) :4799-4802

[8]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[9]

2-Y

[10] Antitumor agents .174. 2',3',4',5,6,7-substituted 2-phenyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization [J].

Chen, K ;

Kuo, SC ;

Hsieh, MC ;

Mauger, A ;

Lin, CM ;

Hamel, E ;

Lee, KH .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (14) :2266-2275

← 1 2 3 4 5 6 →