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微波辐射条件下吡啶-2,6-二甲酸及其衍生物的合成
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摘要
吡啶-2,6-二甲酸,在生物体内是具有生物活性的物质。吡啶-2,6-二甲酸在医学上有着很高的应用价值,吡啶-2,6-二甲酸类稀土配合物倍受关注。它可与镓、铟离子形成稳定的配合物,三种镓配合物对革兰氏阳性菌有明显的抑制作用,其配合物的活性尤为突出,这为进一步考察它们能否用于体外、体内抗癌试验找到了实验基础,为寻找新的抗癌药物提供了重要的理论信息。而聚2,6-P比啶-二甲酸/多壁碳纳米管,可作复合修饰电极等。
     许多吡啶族化合物具有良好的药理活性。据报道从生理上讲吡啶环比苯环更容易被人体所接受,副作用小,因此药物合成中吡啶类杂环药物的设计合成倍受关注。同时吡啶衍生物作为饲料添加剂也很受青睐。
     2,6-吡啶二甲酸二甲酯是一种很重要的吡啶类化合物。研究它的较佳合成方法显得尤为重要。本研究选用在微波辐射条件下,以2,6-二甲基吡啶为原料,合成吡啶-2,6-二甲酸,经酯化后合成2,6-吡啶二甲酸二甲酯。该合成方法尚未见报道。本论文共分为六章:
     第一章以2,6-二甲基吡啶为原料,在微波辐射条件下,通过高锰酸钾氧化合成吡啶-2,6-二甲酸化合物,并分别考察了原料配比、微波辐射功率、辐射时间、硫酸的用量等多种因素对反应的影响,从而优选出较佳反应条件,使合成工艺由传统迈向了新型微波技术。并用~1HNMR、IR表征其结构。
     第二章以吡啶-2,6-二甲酸和甲醇为原料,在波辐射条件下,经酯化后合成了2,6-吡啶二甲酸二甲酯,分别考察了原料配比、微波辐射时间、微波辐射功率、酸度等多种因素对反应的影响,从而优选出较佳反应条件,使合成工艺由传统迈向了新型微波技术。并用~1HNMR、IR表征其结构。
     第三章为了探讨微波辐射条件下2,6-吡啶二甲酰肼的合成工艺,本文研究了微波辐射条件下以吡啶-2,6-二甲酸经酯化,肼解得吡啶-2,6-二甲酰肼。本研究是在微波辐射下通过正交实验,对微波辐射时间、微波辐射温度、配料比及乙醇的用量等因素进行了探索,找到了制备2,6-吡啶二甲酰肼的较佳反应条件。该方法未见文献报道。
     第四章在微波辐射条件下,利用PEG支载的环合剂,以取代苯甲酸和2,6-吡啶二甲酰肼为原料,经一步反应合成2,5-二取代1,3,4-噁二唑类化合物。并分别考察了原料配比、催化剂、微波辐射功率及辐射时间等多种因素对反应的影响,从而优选出较佳反应条件,合成了8中2,5-二取代1,3,4-噁二唑类化合物。用~1HNMR、IR表征其结构,并测定了部分化合物的荧光激发-发射光谱。
     第五章苯巴比妥(Phenobarbital),又名鲁米那,属中枢神经系统药物,为长效巴比妥类,具有镇静、催眠、抗惊厥作用,并可抗癫痫,对癫痫大发作与局限性发作及癫痫持续状态有效。还有增强解热镇痛药之作用,并能诱导肝脏微粒体葡萄糖醛酸转移酶活性,促进胆红素与葡萄糖醛酸结合,降低血浆胆红素浓度,治疗新生儿脑核性黄疸。但目前传统的合成方法比较繁琐,生产成本高,并且使用乙醚容易产生生产事故,生产废液对环境造成一定程度的污染。
     为了降低苯巴比妥的生产成本,简化操作,提高劳动保护,本论文以苯乙酸乙酯为原料,在醇纳催化下,与碳酸二乙酯进行酯缩合后,不经加热脱羧,直接得到2-苯基丙二酸二乙酯而制备苯巴比妥。
     第六章交流示波极谱滴定既有一般物理化学滴定法的优点,又有指示剂滴定法的优点。该方法装置简单、终点直观、操作方便、快速和准确。它比常规指示剂法灵敏度高10倍,广泛用于酸碱、络合、氧化还原和沉淀滴定中,特别适用于药物分析和有机分析。
     本论文提出了用交流示波极谱法测定工业废水中的微量苯酚,并研究了各项试验条件。该法可用于工业废水中微量苯酚的分析测定。
Pyridine-2, 6-dicarboxylic acid, as a compound with biologic activity, plays a great role in the field of medicine. In recent years, the rare metal complexes involving pyridine dicarboxylic acid have received much attention. For example, it can coordinate easily with gallium and indium. And the studies have showed that three Ga(III)-complexes involving pyridine dicarboxylic have significant inhibiting effect on Gram-positive Pathogens, which would help to proving their potentials for some cancers and to synthesizing new anticancer drugs. On the other hand, poly(pyridine-2,6-dicarboxylic acid)/multi-walled carbon nanometer tube can be used as the complex modified electrodes.
     The compounds with a group of pyridine have excellent pharmacologic activities. Up to now, it has increasing interest in the design and synthesis of pharmaceuticals with pyridine ring in the pharmaceutical chemistry, because it was found more absorbable and less side-effects than benzene ring. In addition, the pyridine derivatives have also been used as feed additives.
     2,6—Quinolinic acid dimethyl ester is a kind of pyridine. So, to study a convenient synthetical method is very important. It has not been reported that the goal product is abtained with ethyl benzoic acid as starting material in two steps. This paper consists of six parts.
     Chapter 1: Pyridine dicarboxylic compound was abtained with 2,6-dimethylpyridine as starting material by oxidating of potassium permanganate using microwave irradiation.
     The influences of molar ratio of starting material, power of microwave irradiation, irradiation time and mass fraction of vitriol used were also investigated, and the optimal reaction conditions were found. The goal product was characterized by FT-IR and ~1HNMR.
     Chapter 2: 2,6—Quinolinic acid dimethyl ester was abtained with 2,6—quinolinic acid and methanol as starting material using microwave irradiation. The influences of molar ratio of starting material, power of microwave irradiation, irradiation time and mass fraction of vitriol used were also investigated, and the optimal reaction conditions were found. The goal product was characterized by FT-IR and ~1HNMR.
     Chapter 3: Pyridine-2,6-dicarboxyIic acid hydrazine was synthesized under microwave irradiation. The affects of irradiation time, irradiation power and the ratio of materials on the reaction were discussed, and the optimized reaction conditions were obtained.
     Chapter 4: A series of 2,5-disubstituted 1,3,4-oxadiazoles are synthesized by cyclization of several acids with pyridine-2,6-dicarboxylic acid hydrazine in the presence of a polymer supported cyclizing agent under the silvent-free and microwave irradiation conditions. We studied different affects of varies conditions (ratios, catalysts, irradiation power and time) on the reactions. Then we synthesized 8 2,5-disubstituted 1,3,4-oxadiazoles. The fluorometric spectrum of some compounds is analyzed.
     Chapter 5: Phenobarbital (PB) has been widely using as a prototype inducer for biochemical investigations of drug/ steroid metabolism and the enzymes catalyzing this metabolism. PB is a potentially neuroprotective agent that may prevent ischaemic injury and reduce blood pressure fluctuations and cerebral perfusion in preterm. PB is also the inducer to hepatomicrosome and drug metabolism enzyme. However, the conventional synthetic methods for PB have some disadvantages such as time-consuming, expensive, insecurity from the use of ether, polluted production, and so on.
     In this study the goal product was abtained with ethyl benzoic acid as starting material in two steps in order to reduce the procreative cost
     Chapter 6: AC oscillopolarographic titration was found to be a very useful technique which was convenient, fleetly and veracious, not only in chemistry titration, but also in indicator titration. It is used extensively to acid-base titration, chelatometric titration, oxidation-reduction titration and precipitation titration especially to medicament and organic analysis.
     The application of AC oscillopolarographic method in determination of minim phenol in industrial sewage was studied. The influences of diversified experiment conditions were also investigated. The results showed that this method was feasible in determination of minim phenol in industrial sewage.
引文
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