β-环糊精-丙磺酸催化合成14-烷基(芳基)-14H-二苯并[a,j]氧杂蒽衍生物

Synthesis of 14-Alkyl- or Aryl-14H-Dibenzo[a,j]xanthenes Catalyzed by β-Cyclodextrin-Propyl Sulfonic Acid

摘要:

本文以β-环糊精（β-CD）为原料，在氢氧化钠水溶液中与1,3-丙磺酸内酯反应得到磺酸丙基醚-β-环糊精，再经阳离子交换树脂得到催化剂β-环糊精-丙磺酸（β-CD-PSA）。以苯甲醛和β-萘酚的缩合反应为模板反应，探讨反应温度、催化剂用量对反应的影响并优化工艺条件。以β-CD-PSA/H2O为催化体系，制备了一系列14-烷基（芳基）-14H-二苯并[a,j]氧杂蒽衍生物，β-CD-PSA用量为1 mol%，反应温度为100 ℃，反应时间为6~60 min，反应产率为85~95%。催化剂具有良好的循环使用性能，至少循环使用10次，其催化活性为明显降低。该方法具有操作简单、产率高、反应时间短、环境友好等优点。

Abstract:

β-CD was reacted with 1, 3-propane sultone in NaOH solution to afford sulfopropyl ether β-cyclodextrin, and subsequently, it was further treated with acidic resin to give β-cyclodextrin-propyl sulfonic acid (β-CD-PSA). In order to optimize the conditions, the condensation reaction of benzaldehyde and β-naphthol was examined in presence of different amounts of β-CD-PSA under various reaction conditions. A series of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes were synthesized in presence of 1 mol% of β-CD-PSA, in water at 100 ℃ to afford the corresponding compounds in 85~95% within 6~60 min. The catalyst can be reusable. It could be reused ten-times without a significant loss of catalytic activity. The present protocol offers several advantages, including simple work-up procedure, high yields, short reaction time and benignity procedure.