目录
目录
摘要 Ⅱ
关键词 Ⅱ
Abstract Ⅲ
引言
引言1
1课题背景2
1.1三羰基化合物2
1.2三羰基化合物用于氮杂环的合成3
1.2.1异喹啉衍生物的合成4
1.2.22乙烯基吡咯与4羟基吲哚衍生物4
1.2.3三羰基化合物、胺和酮合成1H吡咯3（2H）酮5
1.3原因及任务6
2方案论证6
2.1三羰基化合物合成方法选择6
2.2氮杂环合成方法的选择7
3过程与分析7
3.1三羰基化合物、炔酯、胺三组分反应的条件优化7
3.1.1实验设计7
3.1.2结果分析9
3.2三羰基化合物的合成9
3.3三羰基化合物、胺、炔酯生成氮杂环的底物适用性研究9
3.3.1合成方法及产率9
3.3.2核磁数据12
3.3.3结果分析13
4讨论与结论14
致谢14
参考文献14
附录16
炔酯、胺及三羰基化合物的三组分反应用于氮杂环的合成研究
摘要
杂环骨架是重要的结构单元，广泛存在于天然产物、药物中，在天然产物化学、药物化学、材料化学、生物化学等领域有着非常广泛的应用。开发各类杂环合成新方法一直是有机化学领域的热点之一，但是很大一部分杂环的合成方法存在一些需要改善的地方，例如反应条件苛刻，使用过渡金属催化剂，产生对环境和人体有危害的副产物等缺陷。本实验旨在开发简便温和的吡咯3酮合成方法，反应无需使用过渡金属催化剂、无有害副产物生成。前期我们开发了三羰基化合物、胺及羰基化合物的三组分反应，成功合成了一系列吡咯3酮衍生物。然而反应仅限于羰基化合物底物，应用范围局限。为拓宽三羰基化合物在吡咯3酮的合成中的应用范围，实现多样性合成，寻找新的反应方式尤为重要。从寻找新的原位生成烯胺的角度出发，本课题拟研究炔烃参与反应的可能性。首先，合成一系列三羰基化合物原料，以此学习三羰基化合物的合成方法，了解三羰基化合物的合成原理 *51今日免费论文网|www.51jrft.com +Q: ^351916072# 
。随后，对三羰基化合物、胺、炔烃三组分反应条件进行探索，找出适合的反应条件。最后对该方法的底物适用性进行研究，探索一系列三羰基化合物、胺及炔酯的反应性能，确定该反应的应用范围及产物产率。
STUDY ON THE SYNTHESIS OF NITROGEN HETEROCYCLES BY THREE COMPONENT REACTIONS OF ALKYNES, AMINES AND TRICARBONYL COMPOUNDS
ABSTRACT
Heterocycles are important skeletons that widely exist in biological active compounds, medicines. They were widely used in pharmaceutical, material industries and in organic synthesis. Thus exploring new methods for the synthesis of heterocycles always remaining one of the hottest areas. However, many existing methods have some limitations such as requiring harsh reaction conditions, using transition metal catalyst, forming toxic byproducts and so on. In this project, we intend to explore an environmental benign, transition metal free and highly efficient method for the synthesis of pyrrole3ones. Previously, we have reported a novel synthesis of pyrrole3ones via three component reactions of tricarbonyl compounds, amines and ketones. Although this strategy can tolerate with very broad substrates while the starting material always limited to ketone. To realize the diversityoriented synthesis, it is necessity to expand the substrate scope of this three component reaction. In order to form the enamines in situ, we intend to study the possibility of using alkynes instead of ketones. At the beginning of the experiment, the synthesis of tricarbonyl compounds is carried out, so as to learn the synthetic method of tricarbonyl compounds and understand the synthesis principle of tricarbonyl compounds. Then, we set out to explore the reaction conditions, the reaction conditions were optimized, and a variety of substances were selected to synthesize Nheterocycles from alkyne esters, amines and tricarbonyl compounds. Lastly, the substrate was expanded, and the synthesis of NHeterocycle was studied by changing the alkyne ester, amine or tricarbonyl compound, keeping other conditions unchanged. The reaction range and product yield were determined. The scope of application of this experiment is not too wide. Only by changing the amines can we get ideal heterocyclic compounds. The products obtained by changing the alkyne ester and the tricarbonyl compound are not theoretical products in the NMR spectrum, and the yield is generally not too high. However, the reaction conditions are not too harsh. The reaction temperature can be controlled at 80 ℃, and the reaction reagent can be obtained and easy to get.

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