Construction Of Pyrrolo[1,2-a][1,10]Phenanthrolines And Dicarbonyl Pyrrolo Based On IMCRs

Multicomponent reactions involving a domino process with at least three different substrates particularly performed under solvent-free or green solvents conditions have emerged as a powerful strategy for the synthesis of chemically and biologically important organic frameworks. This protocol allows molecular complexity approaches the concept of an ideal synthesis.As an important kind of nitrogen-containing heterocycles,1,10-phenanthroline and its derivatives have received great attention in their coordinating with transition metal ions, exhibit pronounced photochemical, electrochemical and biological activities and can be used in many fileds. So far, pyrrolo[1,2-a][1,10]phenanthroline derivatives are promising candiates for solid-state device technology, particularly organic light emitting diodes, no utility as a probe for metal ions has been reported.Due to its janus-faced properties of copper ion in organisms, considerable attention has been devoted to the design of efficient and selective colormetric chemosensors for Cu2+because of its simplicity, quick and nondestructive advantages of the absorption methods.The solvent-free reaction (SFR) is an important synthetic procedure from the view point of green and sustainable chemistry. These approaches can help to reduce the amounts of undesired hazardous chemicals (including solvents) used, increase the selectivity towards the given products, and also enhance the rate of many organic reactions.In the first chapter, we report a one-pot solvent-free reaction based on aldehydes, malononitrile, cyclohexyl or ethyl isocyanoacetate and [1,10] phenanthroline four-component under solvent-free and catalyst-free condition to synthesize pyrrolo[1,2-a][1,10]phenanthroline derivatives. Different electronically substituents of substituted benzaldehyde also had some influence on the yields, particularly for the electronic withdrawing effect. All the isolated products only need washing with ethanol twice rather than column chromatography or recrystallization. In a word, this method was seldom reported with mild condition, simple operation, and rapid reaction, solvent-free and catalyst-free, which was used to synthesize23target compounds5a-5p,6a-6g without using any catalyst or activation. The products preliminarily investigated as chromogenic and fluorescent sensors for Cu2+ions.In the second chapter, we wish to develop a synthetic methodology based on IMCRs to construct a novel small organic fluorescent framework via a one-pot reaction under green solvent with high atom economy. These reactions proceeded in mild conditions and are rapid to execute without using any catalyst or activation. Seven target compounds were synthesized.All products have been characterized by1R,1H NMR,13C NMR and HRMS. And put forward a possible reaction mechanism.