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摘 要：本论文通过选择几种已有文献报道的氮杂环芳香羧酸的合成方法，并设计、合成了一种未见报道的新颖氮杂环芳香羧酸化合物，那就是利用合适的配比合成一种新型的芳基取代吡唑-5-羧酸即3-(2-吡啶基)吡唑-5-羧酸(pypzcH2)，氮杂环芳香羧酸上的氮原子和羧酸上的氧原子可以与许多金属离子配位[1]形成空间结构复杂的多种晶体。常见的芳基为苯基及其衍生物 [2-4]，到目前为止，其他芳基取代的吡唑羧酸的配合物并未见报道。因此，我们想从芳香基的替换上着手考虑新的化合物的合成。我们想要从设计手性合成开始，3-(2-吡啶基)吡唑-5-羧酸(pypzcH2)的合成思路和路线与以往的类似的化合物的合成并不相同，以往合成的吡唑二羧酸大都不具有手性，合成所需要的原料也比较便宜，相对比较容易的得到，手性和非手性的化合物的用途有的大相径庭。而且手性功能化合物远远要比非手性的应用范围广得多，应用价值和作用显得更加重要了。我们都知道乙酰丙酮原料很容易得到也很便宜，乙酰丙酮和水合肼进行亲核加成反应，经过脱水关环生成二甲基吡唑，在酸性高锰酸钾氧化下，甲基被氧化为羧基，最终得到吡唑二羧酸。吡唑环是平面结构，因此是无手性的物质，这类化合物合成的比较多，到目前已经非常成熟了，而考虑把其中的一个羧基换为苯环或者是芳香杂环，则两个环不在同一个平面内，则新合成的化合物就具有了手性。杂环上的杂原子和羧基上的氧原子可以与金属离子进行配位形成多种复杂空间结构的晶体，因此手性功能配合物的合成非常有用，也是目前一大合成研究的热点。因此我们从此类化合物的合成着手也是非常必要和有意义的，思路是我们利用2-乙酰吡啶和乙二酸二乙酯进行亲核加成消除反应，然后再和乙二胺进行脱水关环得到我们想要的具有芳香手性的目标产物3-(2-吡啶基)吡唑-5-羧酸(pypzcH2)。29537
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毕业论文关键词：亲核加成；脱水关环；亲核加成消除反应；手性化合物
The Synthesis And Characterization of 3-(2-pyridyl)-5-pyrazole Carboxylic Acid
Abstract:This paper through the synthesis methods of several heterocyclic aromatic carboxylic acids have been reported and have designed of novel heterocyclic aromatic carboxylic acid compounds，a unreported synthesis，that is using appropriate proportion of synthesisofnovelarylsubstituted pyrazole carboxylic acid-5-3-(2-pyridyl) pyrazole carboxylic acid-5-(pypzcH2)，the nitrogen atom and oxygen atom of carboxylic of heterocyclic aromatic carboxylic acid can match with many metal ions to form a variety of complex crystal space structure．Common for aryl phenyl derivatives，so far，pyrazole carboxylic acid other aryl substituted complexes have not been reported.therefore，we want to consider synthetising new compounds by replacing synthetic aryl．We want to start from the design of chiral synthesis，synthesis method and route of 3-(2-pyridyl)-5-pyrazole carboxylic acid (pypzcH2) is not the same as the similar compounds of previous synthesis of pyrazole carboxylic acid, almos of the synthesis of pyrazole carboxylic acid is not chiral in the past，the raw material needed is relatively cheap，relatively easy to obtain．The use of chiral and nonchiral compounds have much different．But the scope of application of chiral functional compounds are wider than non chiral compounds，and appear more important role and application value．We all know that it is easy and very cheap to get raw materials acetylacetone,acetylacetone and hydrazine hydrate were nucleophilic addition reaction，after dehydration and cyclization to generate two methyl pyrazole, Potassium Permanganate oxidation in acid，methyl is oxidized to carboxyl，obtained two pyrazole carboxylic acid．Pyrazole ring is a planar structure，so it is no chiral substances，up to now these synthesis of compounds have been more and very mature, but consider a change to the carboxyl or heterocyclic aromatic benzene ring，the two rings are not in the same plane，then the synthesis of new compounds is the chiral compounds．The oxygen atoms on the heterocyclic atoms and carboxyl groups on the ligand can match with metal ions and form a variety of complex spatial structure of crystal．so the synthesis of chiral functional complexes is very useful，that is also currently a hot research synthesis．So beginning with the synthesis of compounds is very necessary and meaningful idea，we use 2-acetyl pyridine and oxalic acid ethyl ester by nucleophilic addition elimination reaction，then dehydration cyclization and ethylenediamine，we want the target product with aromatic chiral 3-(2-pyridyl) pyrazolecarboxylic acid-5-(pypzcH2．)
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