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摘要多硝基咪唑化合物一直作为抗生素、放射增敏剂和抗原药研究，主要应用于医药化学领域。然而近年来，人们发现硝基咪唑化合物具有良好的爆炸性能，得到含能材料工作者广泛关注，因此被纳入“高能密度材料”的领域。64335
以4-硝基咪唑为原料，经过卤代、苄基保护N基团和甲胺化得到目标产物。首先4-硝基咪唑与卤素发生亲电取代，结果表明在1.5倍摩尔当量的碱和40℃的条件下溴代反应收率最高，为66%；研究了苄基保护卤代硝基咪唑1位N的反应，结果表明在50℃条件下反应较快，并且因卤代硝基咪唑部分发生异构化，而得到两种同分异构体1-苄基-2,4-二溴-5-硝基咪唑和1-苄基-2,5-二溴-4-硝基咪唑；研究了两种同分异构体与甲胺的亲核取代反应，发现只有1-苄基-2,4-二溴-5-硝基咪唑发生了反应得到了产物；产物经核磁共振和质谱进行了表征。
毕业论文关键字： 硝基咪唑 卤代硝基咪唑 苄基保护 亲核取代
毕业设计说明书（论文）外文摘要
Title Synthesis of halonitroimidazoles and its Derivatives
Abstract Polynitroimidazoles have been investigated mostly due to their properties as antibiotics, radiosensitizers and anti-protozoans and mainly used in medicinal chemistry. However, quite recently, nitroimidazole compounds were found to have good explosive properties, these nitroimidazoles, so it were incorporated into “high energy density materials”.
With 4 - nitro-imidazol as the raw material, after the reaction of halo, benzyl-protected N group and of methylamine, obtained the target product. First step is 4 - nitroimidazole with the halogen reacted in electrophilic substitution, The results show that at 1.5 times the molar equivalent of the base and under the conditions of 40 ℃ the bromination attain the highest yield of 66%; The N-1 reaction of Halonitroimidazole protected by benzyl are studied and the results show that the reaction conditions is fast at 50 ℃. The isomerization of halonitroimidazole will lead to two kinds of isomers :1 - benzyl-2 ,4 - dibromo-5 - nitro-imidazole and 1 - benzyl-2 ,5 - dibromo - 4 - nitro-imidazole; The nucleophilic substitution reaction of this two isomers with methylamine are studied , found that only 1 - benzyl-2 ,4 - dibromo-5 - nitroimidazole is reacted. And the product is characterized by NMR and mass
Keywords nitroimidazole halonitroimidazoles Benzyl protection nucleophilic substitution
1 绪论 5
1.1 咪唑的基本性质 5
1.2 硝基咪唑类化合物简介 5
1.3卤代硝基咪简介 7
1.4 咪唑化合物的基本反应 10
1.5 本文的研究内容 11
2 实验部分 12
2.1 实验条件 12
2.2卤代硝基咪唑及其衍生物的合成 14
结论 20
致谢 21
参考文献 22
1 绪论
多硝基咪唑由于氮原子的电负性较高, 能形成类苯结构的大π键, 具有对静电、摩擦和撞击钝感、热稳定性好的性能,是一类新型优良的不敏感炸药。过去, 硝基咪唑及其衍生物的研究主要集中在医药化学领域。近年来, 国外对1,4—二硝基咪唑(1,4-DN I)、2,4-二硝基咪唑(2,4-DN I)、2,4,5-三硝基咪唑(2,4,5-TN I)等三种合成进行了重点研究。