Intramolecular Heterocyclization of O-Propargylated Aromatic Hydroxyaldehydes as an Expedient Route to Substituted Chromenopyridines under Metal-Free Conditions

被引：70

作者：

Keskin, Selbi ^{[1
]}

Balci, Metin ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

关键词：

PYRIDINE-FUSED COUMARINS; II INHIBITORY-ACTIVITY; BIOLOGICAL EVALUATION; SYNTHETIC APPROACH; TOPOISOMERASE-I; DERIVATIVES; CHROMENE; LIGANDS; SYSTEMS; SERIES;

D O I：

10.1021/acs.orglett.5b00067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by reaction with propargylamine. The intramolecular cycloaddition reaction between the alkyne and azadiene, which is formed as an intermediate, furnished the desired skeletons.

引用

页码：964 / 967

页数：4

共 53 条

[1] Dapson in heterocyclic chemistry, part VIII: synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biologically active 1,3-dihydropyridine, chromene and chromenopyridine moieties [J].

Al-Said, Mansour S. ;

Ghorab, Mostafa M. ;

Nissan, Yassin M. .

CHEMISTRY CENTRAL JOURNAL, 2012, 6

[2] Diversity-oriented synthesis of privileged benzopyranyl heterocycles from s-cis-enones [J].

An, Heeseon ;

Eum, Sung-Jin ;

Koh, Minseob ;

Lee, Sung Kwang ;

Park, Seung Bum .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1752-1761

[3] An expedient synthesis of diversified pyrrolizines and indolizines [J].

Bashiardes, G ;

Safir, I ;

Barbot, F ;

Laduranty, J .

TETRAHEDRON LETTERS, 2004, 45 (07) :1567-1570

[4] New synthetic approach to [1]benzopyrano[4,3-b]pyridin-5-one derivatives [J].

Beccalli, EM ;

Contini, A ;

Trimarco, P .

TETRAHEDRON LETTERS, 2004, 45 (17) :3447-3449

[5] NIR-fluorescent coumarin-fused BODIPY dyes with large Stokes shifts [J].

Bochkov, Andrei Y. ;

Akchurin, Igor O. ;

Dyachenko, Oleg A. ;

Traven, Valery F. .

CHEMICAL COMMUNICATIONS, 2013, 49 (99) :11653-11655

[6] A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids [J].

Brun, MP ;

Bischoff, L ;

Garbay, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3432-3436

[7] Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions [J].

Caporale, Andrea ;

Tartaggia, Stefano ;

Castellin, Andrea ;

De Lucchi, Ottorino .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :384-393

[8] Total Syntheses of the Coumarin-Containing Natural Products Pimpinellin and Fraxetin Using Au(I)-Catalyzed Intramolecular Hydroarylation (IMHA) Chemistry [J].

Cervi, Aymeric ;

Aillard, Paul ;

Hazeri, Nourallah ;

Petit, Laurent ;

Chai, Christina L. L. ;

Willis, Anthony C. ;

Banwell, Martin G. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9876-9882

[9] Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization [J].

Cetinkaya, Yasin ;

Balci, Metin .

TETRAHEDRON LETTERS, 2014, 55 (49) :6698-6702

[10] Synthesis and Properties of Fluorescence Dyes: Tetracyclic Pyrazolo[3,4-b]Pyridine-Based Coumarin Chromophores with Intramolecular Charge Transfer Character [J].

Chen, Jianhong ;

Liu, Weimin ;

Ma, Jingjin ;

Xu, Haitao ;

Wu, Jiasheng ;

Tang, Xianglin ;

Fan, Zhiyuan ;

Wang, Pengfei .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) :3475-3482

← 1 2 3 4 5 6 →