6,6′-Dimethyl-2,2′-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands
6,6′-Dimethyl-2,2′-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands
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DOI：
10.1016/j.tet.2009.06.111
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发表时间：
2009-09-05
期刊：
影响因子：
2.1
通讯作者：
Picard, Claude
中科院分区：
文献类型：
--
作者：
Havas, Fabien;Leygue, Nadine;Picard, Claude
我们描述了一种高效和可扩展的合成4-碳甲氧基-6,6'-二甲基-2,2'-联吡啶的方法，从容易获得的取代的2-卤代吡啶开始，基于改进的根岸交叉偶联条件的应用。该化合物是合成含卤化物、醇、胺和其他官能团的4功能化2,2'-联吡啶的通用起始材料，适用于偶联生物材料（2a-c, 3a-g）。两种双功能镧系螯合剂的合成进一步证明了该化合物在构建更复杂结构中的应用；基于一个2,2'-联吡啶单元的开链配体和基于三个2,2'-联吡啶单元的隐体[N-2(bpy)(3)COOMe]。在致光性生物标签领域，报道了相应的Eu（III）隐泡物的光物理性质。2009爱思唯尔有限公司版权所有。
We describe an efficient and scalable synthesis of 4-carbomethoxy-6,6'-dimetllyl-2,2'-bipyridine starting from easily available substituted 2-halopyridines and based on the application of modified Negishi cross-coupling conditions. This compound is a versatile starting material for the synthesis of 4-functionalized 2,2'-bipyridines bearing halide, alcohol, amine, and other functionalities, suitable for conjugation to biological material (2a-c, 3a-g). The utility of this compound in the construction of more complex architectures was further demonstrated by the synthesis of two bifunctional lanthanide chelators; an open chain ligand based on one 2,2'-bipyridine unit anti a cryptand based on three 2,2'-bipyridine units [N-2(bpy)(3)COOMe]. In the field of luminophoric biolabels, the photophysical properties of the corresponding Eu(III) cryptate are reported. (C) 2009 Elsevier Ltd. All rights reserved.