1,3-双苯基-β-二酮衍生物合成吡唑类衍生物  

Synthesis of Pyrazole Derivatives via 1, 3-Diaryl-β-diketone Derivatives

作　　者：安亚琼 刘振东[1] 刘会影[1] 吴政[1] 侯园园 张艺媛 AN Ya-qiong;LIU Zhen-dong;LIU Hui-ying;WU Zheng;HOU Yuan-yuan;ZHANG Yi-yuan(School of Materials Science and Engineering,Beijing Institute of Fashion Technology,Beijing 100029,China)

机构地区：[1]北京服装学院材料科学与工程学院

出　　处：《北京服装学院学报（自然科学版）》2019年第2期16-22,共7页Journal of Beijing Institute of Fashion Technology：Natural Science Edition

基　　金：国家自然科学基金青年科学基金(21603008);北京市教委科技一般项目(SQKM201610012006);北京服装学院校内人才引进计划(2015A-16)

摘　　要：以人工合成的1,3-双苯基-β-二酮与水合肼进行亲核加成反应,生成吡唑类化合物。实验中发现酸性溶剂下,无法得到吡唑类目标产物,而在碱性催化条件下生成吡唑类衍生物。核磁和质谱表征确认酸性溶剂下产物为2-(4′-二甲氨基苯基)-黄酮,碱性催化条件下为3-(2-羟基苯基)-5-(4-二甲氨基苯基)-1H-吡唑,为目标产物。讨论分析了酸性和碱性条件对反应的影响并探讨了其反应机理,结论为在酸性条件下发生了亲电取代反应,碱性条件下为亲核加成。两种化合物的紫外吸收光谱和荧光光谱会受溶剂极性的影响而发生改变。In this paper, a pyrazole derivative was synthesized from 1, 3-diaryl-β-diketone and hydrazine by nucleophilic addition. Under acidic condition, the product was 2-(4-dimethyl amino phenyl)-flavonoid, not the target product. Under alkaline conditions, the product was 3-(2-hydroxyphenyl)-5-(4-dimethylaminophenyl)-pyrazole, the target product. Both products were confirmed by nuclear magnetic resonance and mass spectrometry. The reaction mechanism under acidic condition is proposed to be electrophilic substitution while that under alkaline condition to be nucleophilic addition. It was found that the uv and fluorescence spectra of the two compounds were affected by the solvent polarity.

关 键 词：酸碱条件 杂环化合物 溶剂极性 

分 类 号：O621.3[理学—有机化学]