Alonso Cristina M A, Serra Vanda I V, Neves Maria G P M S, Tomé Augusto C, Silva Artur M S, Paz Filipe A A, Cavaleiro José A S
Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Org Lett. 2007 Jun 7;9(12):2305-8. doi: 10.1021/ol070601w. Epub 2007 May 17.
Beta-amino-meso-tetraarylporphyrins react with cyclic enol ethers to yield pyrido[2,3-b]porphyrins bearing two vicinal hydroxyalkyl groups. These reactions are catalyzed by lanthanum triflate and occur under mild conditions. Esterification of the hydroxyalkyl groups with succinic anhydride and dodecanoyl chloride afforded the corresponding esters in almost quantitative yields. The crystal structure of the most hydrophobic derivative 7 was determined, and it shows that these porphyrinic macrocycles form one-dimensional supramolecular tapes in the solid state.
β-氨基-中位-四芳基卟啉与环状烯醇醚反应生成带有两个邻位羟烷基的吡啶并[2,3-b]卟啉。这些反应由三氟甲磺酸镧催化，且在温和条件下发生。用琥珀酸酐和十二烷酰氯将羟烷基酯化，几乎以定量产率得到相应的酯。测定了最疏水衍生物7的晶体结构，结果表明这些卟啉大环在固态下形成一维超分子带。
