Wu Xianghong, Gorden Anne E V
Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, 179 Chemistry Building, Auburn, Alabama 36849-5319, USA.
J Comb Chem. 2007 Jul-Aug;9(4):601-8. doi: 10.1021/cc070021q. Epub 2007 May 12.
A solution-phase parallel method for the synthesis of 2-quinoxalinol salen ligands was designed and optimized. The synthesis begins with commercially available 1,5-difluoro-2, 4-dinitrobenzene (DFDNB) and employs a sequence of five straightforward and high-yielding reaction steps. Simple laboratory techniques with low sensitivity to water or air for solution-phase parallel reactions were coupled with convenient workup and purification procedures to give high-purity and yield a small ligand library of 20 compounds. The final step, a Schiff-base condensation of an aldehyde with the diaminoquinoxaline results in a new category of ligands for metal coordination or of potential bioactivity, based on the skeleton 2,2'-(1E,1'E)-(quinoxaline-6,7-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)diphenol. The approach described here is easily adaptable for parallel synthesis of a larger library.
设计并优化了一种用于合成2-喹喔啉醇水杨醛配体的溶液相平行方法。合成从市售的1,5-二氟-2,4-二硝基苯（DFDNB）开始，采用一系列五个直接且高产率的反应步骤。将对溶液相平行反应对水或空气低敏感性的简单实验室技术与便捷的后处理和纯化程序相结合，以获得高纯度并生成一个包含20种化合物的小配体库。最后一步，醛与二氨基喹喔啉的席夫碱缩合反应产生了一类基于骨架2,2'-（1E,1'E）-（喹喔啉-6,7-二基双（氮杂-1-基-1-亚基））双（甲烷-1-基-1-亚基）二苯酚的新型金属配位配体或具有潜在生物活性的配体。这里描述的方法很容易适用于更大文库的平行合成。
