Catalyst-free synthesis of benzofuran-fused pyrido [4,3-d]pyrimidines from 2-(2-hydroxyaryl)acetonitrile and 4,6-dichloropyrimidine-5-carbaldehyde through domino condensation reactions

被引：10

作者：

Li, Bo ^{[1
,2
]}

Yue, Zhizhou ^{[1
]}

Xiang, Haoyue ^{[2
]}

Lv, Linlin ^{[1
]}

Song, Shanshan ^{[2
]}

Miao, Zehong ^{[2
]}

Yang, Chunhao ^{[2
]}

机构：

[1] Wuhan Univ Technol, Sch Chem Engn, Dept Pharmaceut Engn, Wuhan 430070, Hubei, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CASCADE REACTIONS; TOPOISOMERASE-I; INHIBITORS; DISCOVERY; POTENT; ACID; IDENTIFICATION; CONSTRUCTION; DERIVATIVES; ANTITUMOR;

D O I：

10.1039/c3ra44828b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rapid, one-pot, catalyst-free approach to novel benzofuran-fused pyrido[4,3-d]pyrimidines with good antitumor activities via a cascade SNAr/cyclization/condensation reaction through 2-(2-hydroxyphenyl) acetonitriles and 4,6-dichloropyrimidine-5-carbaldehyde was developed.

引用

页码：358 / 364

页数：7

共 38 条

[1] First Intramolecular Alkylation of Nitriles with Primary and Secondary Alcohols Catalyzed by Iridium Complexes [J].

Anxionnat, Bruno ;

Pardo, Domingo Gomez ;

Ricci, Gino ;

Cossy, Janine .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) :4453-4456

[2] A green and facile route to γ- and δ-lactones via efficient Pinner-cyclization of hydroxynitriles in water [J].

Aplander, K ;

Hidestål, O ;

Katebzadeh, K ;

Lindström, UM .

GREEN CHEMISTRY, 2006, 8 (01) :22-24

[3] Selective Synthesis of 1-Substituted 4-Chloropyrazolo[3,4-d]pyrimidines [J].

Babu, Suresh ;

Morrill, Christie ;

Almstead, Neil G. ;

Moon, Young-Choon .

ORGANIC LETTERS, 2013, 15 (08) :1882-1885

[4] Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors [J].

Ball, Catherine J. ;

Willis, Michael C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :425-441

[5] Combining Hit Identification Strategies: Fragment-Based and in Silico Approaches to Orally Active 2-Aminothieno[2,3-d]pyrimidine Inhibitors of the Hsp90 Molecular Chaperone [J].

Brough, Paul A. ;

Barril, Xavier ;

Borgognoni, Jenifer ;

Chene, Patrick ;

Davies, Nicholas G. M. ;

Davis, Ben ;

Drysdale, Martin J. ;

Dymock, Brian ;

Eccles, Suzanne A. ;

Garcia-Echeverria, Carlos ;

Fromont, Christophe ;

Hayes, Angela ;

Hubbard, Roderick E. ;

Jordan, Allan M. ;

Jensen, Michael Rugaard ;

Massey, Andrew ;

Merrett, Angela ;

Padfield, Antony ;

Parsons, Rachel ;

Radimerski, Thomas ;

Raynaud, Florence I. ;

Robertson, Alan ;

Roughley, Stephen D. ;

Schoepfer, Joseph ;

Simmonite, Heather ;

Sharp, Swee Y. ;

Surgenor, Allan ;

Valenti, Melanie ;

Walls, Steven ;

Webb, Paul ;

Wood, Mike ;

Workman, Paul ;

Wright, Lisa .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (15) :4794-4809

[6] Synthesis and SAR development of novel mGluR1 antagonists for the treatment of chronic pain [J].

Brumfield, Stephanie ;

Korakas, Peter ;

Silverman, Lisa S. ;

Tulshian, Deen ;

Matasi, Julius J. ;

Qiang, Li ;

Bennett, Chad E. ;

Burnett, Duane A. ;

Greenlee, William J. ;

Knutson, Chad E. ;

Wu, Wen-Lian ;

Sasikumar, T. K. ;

Domalski, Martin ;

Bertorelli, Rosalia ;

Grilli, Mariagrazia ;

Lozza, Gianluca ;

Reggiani, Angelo ;

Li, Cheng .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (23) :7223-7226

[7] Novel Antitumor Indolizino[6,7-b]indoles with Multiple Modes of Action: DNA Cross-Linking and Topoisomerase I and II Inhibition [J].

Chaniyara, Ravi ;

Tala, Satishkumar ;

Chen, Chi-Wei ;

Zang, Xiuguo ;

Kakadiya, Rajesh ;

Lin, Li-Fang ;

Chen, Ching-Huang ;

Chien, Shin-I ;

Chou, Ting-Chao ;

Tsai, Tung-Hu ;

Lee, Te-Chang ;

Shah, Anamik ;

Su, Tsann-Long .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (04) :1544-1563

[8] One-Pot Transition-Metal-Free Synthesis of Dibenzo[b,f]oxepins from 2-Halobenzaldehydes [J].

Choi, Young Lok ;

Lim, Hye Sun ;

Lim, Hwan Jung ;

Hee, Jung-Nyoung .

ORGANIC LETTERS, 2012, 14 (19) :5102-5105

[9] Synthesis and Biological Evaluation of Indenoisoquinolines That Inhibit Both Tyrosyl-DNA Phosphodiesterase I (Tdp1) and Topoisomerase I (Top1) [J].

Conda-Sheridan, Martin ;

Reddy, P. V. Narasimha ;

Morrell, Andrew ;

Cobb, Brooklyn T. ;

Marchand, Christophe ;

Agama, Keli ;

Chergui, Adel ;

Renaud, Amelie ;

Stephen, Andrew G. ;

Bindu, Lakshman K. ;

Pommier, Yves ;

Cushman, Mark .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (01) :182-200

[10] Pyrazolo-pyrimidines:: A novel heterocyclic scaffold for potent and selective p38α inhibitors [J].

Das, Jagabandhu ;

Moquin, Robert V. ;

Pitt, Sidney ;

Zhang, Rosemary ;

Shen, Ding Ren ;

McIntyre, Kim W. ;

Gillooly, Kathleen ;

Doweyko, Arthur M. ;

Sack, John S. ;

Zhang, Hongjian ;

Kiefer, Susan E. ;

Kish, Kevin ;

McKinnon, Murray ;

Barrish, Joel C. ;

Dodd, John H. ;

Schieven, Gary L. ;

Leftheris, Katerina .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (08) :2652-2657

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