One-pot synthesis of terpyridines and macrocyclization to <i>C</i><sub>3</sub>-symmetric cyclosexipyridines

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<jats:p> Four examples of 2,6-dicinnamoylpyridines were obtained in 60–65% yields in condensations of commercially available 2,6-diacetylpyridine and benzaldehydes in 1:2 stoichiometry. At 2:1 ratios, four related 6,6''-diacetylated-4'-arylterpyridines were isolated in 70–73% yields in one-pot condensations in the presence of NH<jats:sub>3</jats:sub>. 4,4'-Azo benzaldehyde, prepared from nitrobenzaldehyde in three steps and 40% overall yield was similarly converted to a novel azo-linked bis(terpyridine) in 50% yield in a reaction that assembles seven molecules in one step. The 6,6''-diacetylated-4'-arylterpyridines and the correspondingly substituted 2,6-dicinnamoylpyridines were condensed in 1:1 ratio together with NH<jats:sub>3</jats:sub> to form 4,4'',4<jats:sup>IV</jats:sup>-triarylcyclosexipyridines in 22–26% yields. These were obtained as mixed Na<jats:sup>+</jats:sup> and K<jats:sup>+</jats:sup> complexes and were insoluble amorphous solids, except for one example bearing 4-neopentoxyphenyl substituents. <jats:sup>1</jats:sup>H NMR showed that the 4,4'',4<jats:sup>IV</jats:sup>-tri(4-neopentoxyphenyl)cyclosexipyridine complexes form aggregates in solution and at low concentrations show twofold symmetry arising from a loss of planarity.Key words: terpyridines, 4'-aryl-6,6''-diacetylterpyridines, azo-bisterpyridine, cyclosexipyridines, macrocyclization. </jats:p>

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