【作者】 耿亮；

【导师】 王彦广；

【作者基本信息】 浙江大学 ， 化学生物学， 2005， 硕士

【摘要】 杂环化合物具有许多重要的生物活性和药理作用,因此近二十年来一直是有机合成化学和药物化学的研究热点。本论文合成了一系列具有潜在抗菌活性的异(口恶)唑基取代的1,2,4-(口恶)二唑啉和吡唑啉类双杂环类化合物,并发展了一种制备N-芳基咪唑类化合物的新方法,具体内容和结果如下: 1.由3-乙酰基-5-羟甲基异(口恶)唑出发,用硅醚保护羟基,接着与芳香醛反应生成α,β-不饱和酮,再与芳基肼在三乙胺存在下缩合环化,得到了5-(叔丁基二甲基硅氧基甲基)-3-[(1,5-二芳基)-3-(4,5-二氢吡唑基)]一异(口恶)唑类化合物。该方法反应操作简便、产率较高。 2.由3-乙酰基-5羟甲基异(口恶)唑衍生的亚胺与由醛肟原位生成的腈氧化物的1,3-偶极环加成反应制备了5-甲基-5-[5-(叔丁基二甲基硅氧基甲基)-3-异嗯唑基]-3-芳基-4-(4-甲氧基苯基)-4,5二氢-1,2,4-(口恶)二唑,这种方法允许三步反应“一锅”进行,反应条件温和,操作简便。 3.发展了一种微波促进的N-芳基咪唑的合成新方法。在微波辐射、碱和催化量的CuI存在下,咪唑能顺利与卤代芳烃发生N-芳基化反应生成N-芳基咪唑,反应不需加入任何配体,以DMSO做溶剂,反应可在数分钟内完成;此外,在卤代芳烃上有推电子取代基的情况下,反应仍能顺利进行并得到较高的产率。更多还原

【Abstract】 In the last decades, heterocycle compounds have been extensively studied by both organic synthetic chemists and medicinal chemists since a tremendous number of heterocycles have been proven to exhibit biological activities. In this thesis, we synthesized isoxazolyl substituted 1,2,4-oxadiazolines and pyrazolines as potential antibacterial agents, and developed a new method for the synthesis of N-arylimidazoles.1. 5-(tert-Butyldimethylsiloxylmethyl)-3-(1,5-diaryl-4,5-dihydropyrazol-3-yl)isoxaz oles were prepared from 3-acetyl-5-hydroxylmethylisoxazoles in three steps. The protocol gave products in excellent yields and the procedure is facile.2. 5-Methyl-5-[5-(tert-butyldimethylsiloxymethyl)-3-isoxazolyl]-3-aryl-4-(4-methyl oxyphenyl)-4,5-dihydro-1,2,4-oxadiazoles were synthesized via 1,3-dipolar cycloaddition of Schiff bases derived from 3-acetyl-5-hydroxymethyl-isoxazoles and nitrile oxides in situ generated from oximes. This one-pot protocol gave products in good yields and the procedure is very facile.3. A microwave-assisted synthesis of N-arylimidazoles was developed. The TV-arylation reaction between with imidazole and aryl halide in the presence of catalytic amount of Cul could be promoted efficiently by microwave irradiation. The reaction performed in DMSO without any ligant. Electron-rich group substituted aryl halides also gave good yields using this protocol.更多还原