Synthesis of new bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites

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• 作者：Antonio Fern&#xe1 ; ndez-Mato ; Gerardo Blanco ; Jos&#xe9 ; M. Quintela ; Carlos Peinador
• 关键词：Austria ; Slovakia ; Renewables
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：14 April 2008
• 卷：64
• 期：16
• 页码：3446-3456
• 文件大小：551 K

摘要

A series of new 2-[1,8]naphthyridinyl and bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites were prepared using 2-amino-5-cyano-6-ethoxy-4-phenyl-3-carbaldehyde pyridine as excellent Friedländer synthon. Condensation with a series of acetyl(heteroaryl)aromatics provides the corresponding 2-aryl(heteroaryl)-1,8-naphthyridines. Reaction with 1,3-diacetylbenzene, 2,6-diacetylpyridine or 4-tert-butyl-2,6-diacetylpyridine provides the expected Friedländer product. Similar 2:1 condensation with 1,4-diacetylbenzene, 4,4′-diacetylbiphenyl, 1,4- and 1,6-diacetylpyrene, 2,6-diacetylpyrazine or 2,3-butanedione leads to a family of six new bis-1,8-nap ligands. The reaction with cyclic 1,2- or 1,3-diketones affords 3,3′-annelated derivatives of all-syn or all-trans planar 2,2′-nap, respectively. Examination of the electronic absorption and emission spectra of the bridging ligands was realized.