【作者】 施红；

【导师】 朱红军；

【作者基本信息】 南京工业大学 ， 有机化学， 2006， 硕士

【摘要】 近年来,含氮的杂环化合物在医药和农药的研究开发中占据了越来越重要的地位。在这些化合物中,吡唑类的化合物,尤其是吡唑类的芳环化合物被发现有着广泛的生物活性,因此成为了重要的药物研究先导结构,在很多有机合成及生物代谢过程中起着承上启下的中间体作用。糖酯类是人类生存的必不可少的营养物质,并具有广泛的生理活性。已证实,葡萄糖苷杂环类化合物具有抑制肿瘤的活性。在本文中,设计合成了1,5-二芳基-3-吡唑烷酮化合物、1,5-二芳基-3-吡唑烷酮化合物和3-(2,3,4,6-四乙酰基-β-D-吡喃葡萄糖-1-基)-1,5-二芳基吡唑化合物。以3-芳基-2-丙烯酸酯为原料,与芳基肼在醇钠的催化作用下,反应可以生成1,5-二芳基-3-吡唑烷酮,产率在55%以上。所合成得到的产品——1-苯基-5-(3,4,5-三甲氧基苯基)-3-吡唑烷酮、1-苯基-5-(4-溴苯基)-3-吡唑烷酮、1-( 4-氟苯基)-5-(4-甲氧基)-3-吡唑烷酮经元素分析、IR、1H-NMR、晶体结构分析等表征,证明所合成的结构与预期结构相符。经过溶剂缓慢挥发,得到了1-苯基-5-( 4-甲氧基苯基)-3-吡唑烷酮(单斜晶系,空间群为P2(1)/n)、1-苯基-5-( 4-氯苯基)-3-吡唑烷酮(单斜晶系,空间群为P2(1)/C)、1-( 4-氟苯基)-5-(4-甲氧基)-3-吡唑烷酮(单斜晶系,空间群为P2(1)/C)、1-苯基-5-( 4-甲基苯基)-3-吡唑烷酮(三斜晶系,空间群为P-1)的单晶,并进行了晶体结构分析。1,5-二芳基-3-吡唑烷酮在N,N’-二甲基甲酰胺溶液中,在FeCl3.6H2O的催化作用下,由空气中的氧气氧化得到1,5-二芳基-1H-3-羟基吡唑,产率在80%以上。所合成得到的产品———1-苯基-5-(3,4,5-三甲氧基苯基)-1H-3-羟基吡唑、1-苯基-5-(4-溴苯基)-1H-3-羟基吡唑、1-( 4-氟苯基)-5-(4-甲氧基苯基)-1H-3-羟基吡唑经元素分析、IR、1H-NMR等分析,证明所合成的结构与预期结构相符。另外,我们利用在线红外对反应过程进行跟踪,进一步了解了该反应进程。1,5-二芳基-1H-3-羟基吡唑在氯仿-水体系下,四丁基溴化铵为相转移催化剂的催化作用下,与乙酰溴葡萄糖反应,生成3-(2,3,4,6-四乙酰基-β-D-吡喃葡萄糖-1-基)-1,5-二芳基吡唑,一次重结晶的产率在30%左右。所合成的3-(2,3,4,6-四乙酰基-β-D-吡喃葡萄糖-1-基-1-苯基-5-(4-甲氧基苯基)-1H-吡唑、3-(2,3,4,6-更多还原

【Abstract】 Nowadays, Heterocyclic compounds have been developed most quickly and have become the new trend in the development. Among them, pyrazole and its derivatives play an important part, exhibit better bioactivity and are becoming one kind of the most important leading structures in the fields of the organic synthesis. It is known that glucose existed in nature is an important monosaccharose which has a close connection with life phenomena. It has been proved to possess antitumor activities by being incorporated with other heterocyclic compounds. In this thesis, 1, 5-diaryl-3-pyrazilidinones, 1, 5-diaryl-3-hydroxypyrazoles and 3-(2, 3, 4, 6-tetraacetyl-β-D-glucopyranos-1-yl)-1, 5-diaryl-1H-pyrazoles are designed and synthesized.1, 5-diaryl-3-pyrzolidinones were obtained by condensation of 3-arylpropenates and phenylhydrazine or fluorophenylhydrazine under the catalysis of sodium methylate and the yields were about 55-80%. Their structures have been confirmed by elemental analysis, IR, 1H-NMR, single crystal analysis, which showed that the structures of these compounds were the same as desired. Furthermore, the single crystals of 5-(4-methoxylphenyl)-1-phenyl-3-pyrazolidinone (monoclinic, space group P2(1)/n), 5-(4-chlorophenyl)-1-phenyl-3-pyrazolidin(monoclinic, space group P2(1)/c), 5-(4-methoxylphenyl)-1-(4-fluorophenyl)-3-pyrazolidinone(monoclinic, space group P2(1)/c), 5-(4-methylphenyl)-1-phenyl-3-pyrazolidinone(triclinic, space group P-1) were obtained by slow evaporation of an ethanol solution and the crystal structures were characterized.1, 5-diaryalpyrazolidinones were oxidized by oxygen of air in DMF, catalyzed by ferrous chloride, which gained 1, 5-diaryl-1H-3-hydroxypyrazol.Their yields were about 85%. The structures of these products have been confirmed by elemental analysis, IR, 1H-NMR, which showed that the structures of these compounds were the same as desired. Furthermore, the mechanism of the reaction was studied by ReactIR更多还原