Gerkensmeier T, Mattay J, Näther C
Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Germany.
Chemistry. 2001 Jan 19;7(2):465-74. doi: 10.1002/1521-3765(20010119)7:2<465::aid-chem465>3.0.co;2-a.
A new type of calixarene has been synthesised. Like resorcinol and a number of resorcinol derivatives, 2,6-dihydroxypyridine has been proven to form cyclic tetramers in moderate yields with a number of aliphatic and two aromatic aldehydes in acidic media. The problem of the formation of configurational isomers can be reduced by increasing the reaction temperature and time. With electron-rich aromatic aldehydes, 2,6-dihydroxypyridine unexpectedly yields deep-coloured acyclic quinoid systems. The octahydroxypyridine[4]arenes may have a high potential as receptors for molecular recognition and self organisation.
一种新型杯芳烃已被合成。与间苯二酚及多种间苯二酚衍生物一样，已证明2,6 - 二羟基吡啶在酸性介质中能与多种脂肪醛和两种芳香醛以中等产率形成环状四聚体。通过提高反应温度和时间，构型异构体形成的问题可以得到缓解。对于富电子芳香醛，2,6 - 二羟基吡啶意外地生成深色的无环醌类体系。八羟基吡啶[4]芳烃作为分子识别和自组装的受体可能具有很高的潜力。
