【作者】 李秋莲；

【导师】 朱永明；

【作者基本信息】 苏州大学 ， 药物化学， 2011， 硕士

【摘要】 黄酮和异黄酮类化合物具有广泛而重要的生物活性和药理活性,例如抗癌,抗炎,抗肝脏毒性等。其化学合成研究受到普遍重视。近年来,随着铜催化的碳-氮偶联氨基化反应以及串联反应的广泛研究及报道,本课题组也采用铜催化串联缩合-环化反应合成了吡唑并[1, 5-a]喹啉和吡唑并[1, 5-a]吲哚类等化合物。鉴于此,我们探索利用铜催化的碳-氧键分子内环化反应来合成黄酮及异黄酮类化合物。结果表明,以取代1-(2-卤素苯基)-丙烷-1, 3-二酮为原料,在[DMSO/K2CO3/130℃/8h]无金属催化的条件下,进行分子内环合反应得到17个黄酮类化合物。采用取代3-(2-卤素苯基)-3-氧-丙醛为原料,在[CuI/2-吡啶甲酸/K2CO3/DMF/135-140℃/20h]条件下,进行分子内环合反应得到了13个异黄酮类化合物。更多还原

【Abstract】 Flavones and isoflavones are a group of naturally occurring compounds that widely distributed in the plant kingdom, and have been associated with a wide variety of biological and pharmaceutical activities, including antitumoral, antiviral, antiin?ammatory, antioxidant, hepatoprotective, and antithrombotic actions. Inspired by reports of Cu(I)-catalyzed intermolecular C-N coupling reaction, we use a novel method of Cu(I)-catalyzed intramolecular amination reaction to synthesize pyrazolo[1, 5-a]indole derivatives and pyrazolo[1, 5-a]quinoline derivatives. Based on the study, we are thinking about using a novel method of Cu(I)-catalyzed intramolecular C-O cyclization reaction to synthesize flavone and isoflavone derivatives.As a result, we found that flavones were developed by intramolecular C-O cyclization reaction under the condition of [DMSO/K2CO3/130℃/8h] starting from 1-(o-halophenyl)-propane-1, 3-diones. And isoflavones were obtained by using commercially available copper (I) iodide as an effective catalyst under the condition of [CuI/2-picolinic acid/K2CO3/DMF/135-140℃/20h] starting from various 3-(2-halo phenyl)-3-oxopropanals.更多还原