镍催化下嘧啶类杂环化合物的合成
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摘要
在医药和农药的研究和开发中,含氮杂环化合物发挥着重要作用,尤其是多取代的嘧啶类杂环化合物更是得到了广泛的应用。做为一个重要的生物内源物质,嘧啶杂环广泛存在于生物体内参与生命活动。含有嘧啶环的新研制的众多化合物也具有生物活性,其化学结构与生物活性之间的关系,主要体现在嘧啶环不同位置的取代基所产生的影响。如近年来报道合成的杂环化合物二氢嘧啶类的衍生物具有抗高血压的生物活性,还有一些C-5、C-6取代的嘧啶类衍生物体现出很好的抗病毒和抑制细胞再生的活性。含有嘧啶杂环的化合物也存在于自然界,他们在一些药物中发挥着重要作用,具有潜在的生物活性,近年来关于此类物质的研究日趋活跃。
本文对近年来嘧啶类杂环化合物的研究进展作了较为详细的综述,并对嘧啶类杂环化合物的合成进行了研究,优化和发展了一种合成嘧啶类杂环化合物的新方法。
本论文共分两章:
第一章:文献综述嘧啶类杂环化合物的研究进展本章对近年来嘧啶类杂环化合物在应用和合成两方面作了较详细的综述。嘧啶类杂环化合物的应用主要体现在农药和医药应用两方面,而嘧啶类杂环化合物的合成主要介绍了嘧啶类杂环化合物的一般合成方法、嘧啶类杂环化合物的其它合成方法和利用Biginelli反应一锅法合成嘧啶类杂环化合物。
第二章:嘧啶类杂环化合物的合成
本章依据Biginelli反应,以乙醇为溶剂,NiCl2·6H2O和浓HCl(aq)分别催化下,采
为了进行目标分子(一)的合成,我们查阅了近年来嘧啶类杂环化合物的各种合成文献,并结合本研究室当前的研究成果,最终用简单易得的原料,采用多组分一锅法,经廉价催化剂NiCl2·6H2O催化合成了30个嘧啶类杂环化合物,并且优化和完善了其合成方法。
在成功地制备出苯并杂环类物质(一)后,目标分子(二)的合成,最初试图也在路易斯酸催化下,通过苯并噻唑与芳醛、1,3-二羰基酯一锅法缩合来合成,但没有取得成功,这可能是由于苯并噻唑的活性差所致。后来,结合这类反应的特点和反应物的结构,我们依然在乙醇中,用催化量的浓盐酸作催化剂,采用一锅法成功的合成了9个新化合物。
本章通过对目标化合物的合成研究,成功地合成出了两大系列结构新颖的苯并嘧啶类杂环化合物,并且逐一对其进行了结构表征,为这类化合物的合成及进一步的性质研究提供了有价值的参考和理论数据。
In the research and exploitation of medicine and pestcide, heterocyclic compounds containing nitrogen play an important role, especially the multi-substituted pyrimidine heterocyclic compounds is widely used. Be used as an important inside source material of the life-form, the miscellaneous pyrimidine ring exists in the inside of the living creature body extensively and participate into the life activity. Meantime, lots of new compounds containing pyrimidine-cycle own potential bioactivity. The relation between their chemical structure and biological activity is depended on affect of substituents in different position of pyrimidin ring. For instance, 4-dihydropyrimidine analogues exhibit good antihypertensive activity, some C-5 and/or C-6 substituted pyrimidine derivatives show good antiviral and cytostatic activities. The compounds, whose structures contain heterocyclic, exist in nature wildly, and they play an important role in many pharmaceuticals, therefore they maybe have potential bioaetivity, the researeh on them is hot.
In this paper, we made a detailed overview on pyrimidine heterocyclic compounds in recent researches, and studied the synthesis of pyrimidine heterocyclic compounds, optimized and developed a new method of synthesis on pyrimidine heterocyclic compounds.
The thesis includes two chapters.
Chapter one: Literature review Research on pyrimidine heterocyclic compounds.
We made a detailed review on both synthesis and application of pyrimidine heterocyclic compounds in recent years in this chapter. Application of pyrimidine heterocyclic compounds is mainly reflected in pesticide and pharmaceutical, the synthesis of pyrimidine heterocyclic compounds, we introduced the general synthesis of pyrimidine heterocyclic compounds, other synthesis of pyrimidine heterocyclic compounds and the synthesis of one-pot Biginelli reaction of pyrimidine heterocyclic compounds.
Chapter two: The synthesis of pyrimidine heterocyclic compounds.
Based on biginelli reaction, this chapter wish to report catalytic amount of NiCl2·6H2O and concentrated hydrochloric acid (HCl) catalyzed three-component condensation respectively for the synthesis of two categories highly substituted pyrimidine heterocycles in one pot.
In order to research the synthesis of target molecular(Ⅰ), We reviewed the recent years literature of synthesis on pyrimidine heterocyclic ccompounds, combined with results of current research in our laboratory, 30 derivates were prepared successfully from inexpensive and ease materials by one-pot multi-component, and the synthesis method of the nitrogen-containing benzoheterocyclic compound(Ⅰ) was optimized.
After benzoheterocyclic compounds(Ⅰ) were prepared successfully, in order to synthesize target molecular(Ⅱ), At first, the attempt of synthesize TM by one-pot condensation reaction between aromatic aldehydes, 1,3-dicarbonyl compounds and benzo[d]thiazol-2-amine in alcohol catalyzed by Lewis acid is failure, which is probably dueto the low reactivity of the benzo[d]thiazol-2-amine. After that, considered the properties of materials and the structures of reactants, 9 novel target compounds were successfully synthesized in one pot catalyzed by catalytic amount of concentrated hydrochloric acid (HCl) in alcohol.
After such research work,two categories novel prymidine heterocyclic compounds have designed and synthesized sueeessfully, and that we tested their structure, explored their characteristics using quantum chemical calculation. Which would provide helpful information for the further studies on these compounds.
本文对近年来嘧啶类杂环化合物的研究进展作了较为详细的综述,并对嘧啶类杂环化合物的合成进行了研究,优化和发展了一种合成嘧啶类杂环化合物的新方法。
本论文共分两章:
第一章:文献综述嘧啶类杂环化合物的研究进展本章对近年来嘧啶类杂环化合物在应用和合成两方面作了较详细的综述。嘧啶类杂环化合物的应用主要体现在农药和医药应用两方面,而嘧啶类杂环化合物的合成主要介绍了嘧啶类杂环化合物的一般合成方法、嘧啶类杂环化合物的其它合成方法和利用Biginelli反应一锅法合成嘧啶类杂环化合物。
第二章:嘧啶类杂环化合物的合成
本章依据Biginelli反应,以乙醇为溶剂,NiCl2·6H2O和浓HCl(aq)分别催化下,采
为了进行目标分子(一)的合成,我们查阅了近年来嘧啶类杂环化合物的各种合成文献,并结合本研究室当前的研究成果,最终用简单易得的原料,采用多组分一锅法,经廉价催化剂NiCl2·6H2O催化合成了30个嘧啶类杂环化合物,并且优化和完善了其合成方法。
在成功地制备出苯并杂环类物质(一)后,目标分子(二)的合成,最初试图也在路易斯酸催化下,通过苯并噻唑与芳醛、1,3-二羰基酯一锅法缩合来合成,但没有取得成功,这可能是由于苯并噻唑的活性差所致。后来,结合这类反应的特点和反应物的结构,我们依然在乙醇中,用催化量的浓盐酸作催化剂,采用一锅法成功的合成了9个新化合物。
本章通过对目标化合物的合成研究,成功地合成出了两大系列结构新颖的苯并嘧啶类杂环化合物,并且逐一对其进行了结构表征,为这类化合物的合成及进一步的性质研究提供了有价值的参考和理论数据。
In the research and exploitation of medicine and pestcide, heterocyclic compounds containing nitrogen play an important role, especially the multi-substituted pyrimidine heterocyclic compounds is widely used. Be used as an important inside source material of the life-form, the miscellaneous pyrimidine ring exists in the inside of the living creature body extensively and participate into the life activity. Meantime, lots of new compounds containing pyrimidine-cycle own potential bioactivity. The relation between their chemical structure and biological activity is depended on affect of substituents in different position of pyrimidin ring. For instance, 4-dihydropyrimidine analogues exhibit good antihypertensive activity, some C-5 and/or C-6 substituted pyrimidine derivatives show good antiviral and cytostatic activities. The compounds, whose structures contain heterocyclic, exist in nature wildly, and they play an important role in many pharmaceuticals, therefore they maybe have potential bioaetivity, the researeh on them is hot.
In this paper, we made a detailed overview on pyrimidine heterocyclic compounds in recent researches, and studied the synthesis of pyrimidine heterocyclic compounds, optimized and developed a new method of synthesis on pyrimidine heterocyclic compounds.
The thesis includes two chapters.
Chapter one: Literature review Research on pyrimidine heterocyclic compounds.
We made a detailed review on both synthesis and application of pyrimidine heterocyclic compounds in recent years in this chapter. Application of pyrimidine heterocyclic compounds is mainly reflected in pesticide and pharmaceutical, the synthesis of pyrimidine heterocyclic compounds, we introduced the general synthesis of pyrimidine heterocyclic compounds, other synthesis of pyrimidine heterocyclic compounds and the synthesis of one-pot Biginelli reaction of pyrimidine heterocyclic compounds.
Chapter two: The synthesis of pyrimidine heterocyclic compounds.
Based on biginelli reaction, this chapter wish to report catalytic amount of NiCl2·6H2O and concentrated hydrochloric acid (HCl) catalyzed three-component condensation respectively for the synthesis of two categories highly substituted pyrimidine heterocycles in one pot.
In order to research the synthesis of target molecular(Ⅰ), We reviewed the recent years literature of synthesis on pyrimidine heterocyclic ccompounds, combined with results of current research in our laboratory, 30 derivates were prepared successfully from inexpensive and ease materials by one-pot multi-component, and the synthesis method of the nitrogen-containing benzoheterocyclic compound(Ⅰ) was optimized.
After benzoheterocyclic compounds(Ⅰ) were prepared successfully, in order to synthesize target molecular(Ⅱ), At first, the attempt of synthesize TM by one-pot condensation reaction between aromatic aldehydes, 1,3-dicarbonyl compounds and benzo[d]thiazol-2-amine in alcohol catalyzed by Lewis acid is failure, which is probably dueto the low reactivity of the benzo[d]thiazol-2-amine. After that, considered the properties of materials and the structures of reactants, 9 novel target compounds were successfully synthesized in one pot catalyzed by catalytic amount of concentrated hydrochloric acid (HCl) in alcohol.
After such research work,two categories novel prymidine heterocyclic compounds have designed and synthesized sueeessfully, and that we tested their structure, explored their characteristics using quantum chemical calculation. Which would provide helpful information for the further studies on these compounds.
引文
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