苯并吖啶類(benzo[b]acridine)和苯并萘氮雜類(benzo[b]naphtha[2,3-f]azepine)的醌類化合物擁有多種的生物活性，包含抗菌、抗病毒、抗腫瘤等作用，目前合成苯并吖啶類化合物的方法有許多，但合成苯并萘氮雜類化合物的方法較少。在此我們嘗試利用銅(II)和銀離子(II)發展出新的合成方法來合成苯并吖啶類(benzo[b]acridine)和苯并萘氮雜類(benzo[b]naphtha[2,3-f]azepine)的醌類化合物。
本篇論文主要分三個部分：
(1) 利用氯化銅(II)進行氧化性環合反應，將2-[(2’-苯乙烯基)苯胺基]-1,4-萘醌化合物合成苯并吖啶類化合物。
(2) 利用氯化銅(II)進行親電性環合反應，將2-[(2’-苯乙炔基)苯胺基]-1,4-萘醌化合物和2-[(2’-乙炔基)苯胺基]-1,4-萘醌化合物合成苯并
萘氮雜類化合物，若是以化合物2-[(2’-苯乙炔基)苯胺基]-1,4-萘醌化合物來進行反應，則會伴隨有
五員環或非環合的副產物。。
(3) 利用硝酸銀(I)搭配過硫酸根離子於水溶液系統生成銀離子(II)進行氧
化性自由基反應，將2-[(2’-苯乙炔基)苯胺基]-1,4-萘醌化合物合成
12-醯基-苯并吖啶類化合物。

Benzo[b]acridines and benzo[b]naphtha[2,3-f]azepines have been found to possess broad
biological activities, such as antifungal, antivirus and antitumor. Benzo[b]acridines and
benzo[b]naphtha[2,3-f]azepines skeleton has also attracted considerable attention in the
literature and several pathways have been developed for its synthesis. In this thesis, we apply
copper(II) to develop a novel route for synthesis of benzo[b]acridines and benzo[
b]naphtha[2,3-f]azepines, and apply silver(II) for synthesis of benzo[b]acridines. Although
the reaction for synthesis of benzo[b]naphtha[2,3-f]azepines with copper(II) accompany
by five-membered ring or non-cyclized byproducts, the total yield is still good.

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