CAJ | 학술논문

以间氨基苯酚和溴代异戊烯为起始原料经过亲核取代制备了N,N-二(3-甲基-2-丁烯)-3-羟基苯胺氢溴酸盐，通过亲电取代关环合成了8-羟基-1,1,7,7-四甲基久洛尼定，再经Vilsmeir-Haack反应引入醛基获得了9-甲酰基-8-羟基-1,1,7,7-四甲基久洛尼定，总收率为25.7%。对N,N-二(3-甲基-2-丁烯)-3-羟基苯胺氢溴酸盐的合成进行了工艺探索，结果表明当间氨基苯酚和溴代异戊烯投料比为1：2，CaCO3为缚酸剂时得到的收率较佳。以9-甲酰基-8-羟基-1,1,7,7-四甲基久洛尼定为原料，分别与噻吩乙腈、对溴苯乙腈进行缩合反应制备得到3-芳基香豆素衍生物，对其结构进行了核磁鉴定，并对其紫外光谱进行了测试。
이간안기분분화추대이무희위기시원료경과친핵취대제비료N,N-이(3-갑기-2-정희)-3-간기분알경추산염，통과친전취대관배합성료8-간기-1,1,7,7-사갑기구락니정，재경Vilsmeir-Haack반응인입철기획득료9-갑선기-8-간기-1,1,7,7-사갑기구락니정，총수솔위25.7%。대N,N-이(3-갑기-2-정희)-3-간기분알경추산염적합성진행료공예탐색，결과표명당간안기분분화추대이무희투료비위1：2，CaCO3위박산제시득도적수솔교가。이9-갑선기-8-간기-1,1,7,7-사갑기구락니정위원료，분별여새분을정、대추분을정진행축합반응제비득도3-방기향두소연생물，대기결구진행료핵자감정，병대기자외광보진행료측시。
N,N-Bis (3-methyl-2-butene)-3-hydroxyanilin hydrobromide was prepared from m-aminophenol and 1-bromo-3-methyl-2-butene via nucleophilic substitution reaction at first. Then 8-hydrox-y-1,1,7,7-tetramethyljulolidine was synthesized by electrophilic substitution. And aldehyde group was intro-duced to prepare 9-formyl-8-hydroxy-1,1,7,7-tetramethyljulolidine through Vilsmeir-Haack reaction. Reac-tion conditions for synthesis of N,N-bis (3-meyhyl-2-butene)-3-hydroxyanilin hydrobromide was explored, and the results showed that when the ratio of m-aminophenol and 1-bromo-3-methyl-2-butene was 1:2 and calcium carbonate was used as acid-binding agent, the yield was optimum. Then 9-formyl-8-hydroxy-1,1,7,7-tetramethyljulolidine reacted with 2-thiopheneacetonitrile or 4-bromophenylacetonitrile to prepare two 3-arylcoumarin derivatives. The structure of the derivative and products were identified by 1H NMR spectroscopy. And the UV spectra of target products were tested.