Synthesis of a halo-methylphenylene periphery-functionalized triazine-based dendritic molecule with a 3,3′-dimethyl-biphenyl linker using tris(halo-methylphenylene)triazines as building blocks

被引:5
作者
Kostas, Ioannis D. [1 ]
Andreadaki, Fotini J. [1 ]
Medlycott, Elaine A. [2 ]
Hanan, Garry S. [2 ]
Monflier, Eric [3 ]
机构
[1] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, Athens 11635, Greece
[2] Univ Montreal, Dept Chim, Montreal, PQ H3T 1J4, Canada
[3] Univ Artois, UMR 8181, Unite Catalyse & Chim Solide, Lens, France
关键词
Dendrimer; Triazine; Cyclotrimerization; Suzuki coupling; Phosphine oxide; Hydroformylation; IN-VIVO TOXICITY; DRUG-DELIVERY; LIQUID-CRYSTALLINE; DENDRIMERS; MELAMINE; HYDROFORMYLATION; PHOSPHINE; CATALYSIS; LIGANDS; OXIDE;
D O I
10.1016/j.tetlet.2009.02.011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tris(bromo-methylphenylene)triazine and its corresponding phosphine oxide derivative have been synthesized; the latter compound was found to be a potent ligand for the hydroformylation reaction. Suzuki coupling of the mono-pinacolboronate derivative of the former compound with a tris(iodo-methylphenylene)triazine was possible at two of the three iodine atoms, yielding a bromo- and iodo-methylphenylene periphery-functionalized triazine-based dendritic molecule with a 3,3 '-dimethyl-bipheny) linker. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1851 / 1854
页数:4
相关论文
共 41 条
[1]   PHOSPHINE VS PHOSPHINE OXIDE LIGANDS IN HYDROFORMYLATION REACTIONS [J].
ABUGNIM, C ;
AMER, I .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :115-117
[2]   Phosphine oxides as ligands in the hydroformylation reaction [J].
AbuGnim, C ;
Amer, I .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 516 (1-2) :235-243
[3]  
[Anonymous], 2001, Dendrimers and Dendrons: Concepts, Synthesis, Applications
[4]   Dendritic catalysts and dendrimers in catalysis [J].
Astruc, D ;
Chardac, F .
CHEMICAL REVIEWS, 2001, 101 (09) :2991-3023
[5]   HYDROFORMYLATION OF SOME FUNCTIONALIZED OLEFINS CATALYZED BY RHODIUM(I) COMPLEXES WITH PYDIPHOS AND ITS P-OXIDE [J].
BASOLI, C ;
BOTTEGHI, C ;
CABRAS, MA ;
CHELUCCI, G ;
MARCHETTI, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 488 (1-2) :C20-C22
[6]   Cytotoxicity, hemolysis, and acute in vivo toxicity of dendrimers based on melamine, candidate vehicles for drug delivery [J].
Chen, HT ;
Neerman, MF ;
Parrish, AR ;
Simanek, EE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :10044-10048
[7]   Kilogram-scale synthesis of a second-generation dendrimer based on 1,3,5-triazine using green and industrially compatible methods with a single chromatographic step [J].
Chouai, Abdellatif ;
Simanek, Eric E. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2357-2366
[8]   A divergent route towards single-chemical entity triazine dendrimers with opportunities for structural diversity [J].
Crampton, Hannah ;
Hollink, Emily ;
Perez, Lisa M. ;
Simanek, Eric E. .
NEW JOURNAL OF CHEMISTRY, 2007, 31 (07) :1283-1290
[9]  
Frechet J.M, 2001, Dendrimers and Other Dendritic Polymers
[10]  
FREEMAN AW, 1997, POLYM MAT SCI ENG, V77, P138