Synthesis Of Indole, Pyrrole And Pyrimidine Compounds

Nitrogen-containing heterocyclic compounds are widely distributed in nature,rich in variety,and most of them have display a diverse range of biological activities,as well as some special properties,such as fluorescence,conductivity,etc.As a result,they have some remarkable applications in medicine,agriculture,materials and supramolecular and others,especially have also been received much attention in organic synthesis in recent years.Among them,indoles and pyrroles in particular draw researchers' attention because of most of them possess a broad range of pharmacological activities,such as antibacterial,anti-tumor,anti-inflammatory activities.In addition,the pyrimidines are also an important class of nitrogen-containing heterocycles in the organic synthesis,these compounds have exposed a considerable number of potential biological activities,such as antimicrobial,antioxidant,insecticidal,etc.,additionally,they can serve as many drug molecules,macromolecules synthesis Intermediates,resulting in they have acted as many important roles in pesticides,biological and organic synthesis.Although tremendous synthetic methods for the synthesis of indoles,pyrroles,pyrimidines and their derivatives have been developed,established,and reviewed,most of the synthesis methods are sometimes harsh,complicated,and often restricted owing to the lack of substrate availability.Consequently,the development of atom-economical and efficient methods to synthesize diverse heterocyclic compounds with potentially pharmacologically activities is of great significance.Accordingly,this article carried out the following work:In the first chapter,the researchs on nitrogen-containing heterocyclic compounds,indoles,pyrroles and pyrimidines are briefly reviewed.In the second chapter,an efficient one-pot method was developed for the synthesize of a series of novel highly functional indole compounds II-4 by employing the heterocyclic ketene aminals 1 and the readily available o-difluorobenzene derivative ?-2 as the raw materials and using 1,4-dioxane as the solvent under alkaline conditions(K2CO3 or Cs2CO3),the yield was 85%-97%.In the third chapter,we have developed a concise and practical method for to synthesize indenopyrroles(?-6 and ?-7)that have not been reported by mixing with nitro-enamine(?-3 or ?-4)and ninhydrin with ethanol as solvent,with the excellent yields of 91%-98%.The nitroenamine(?-3 or ?-4)were fully prepared according to reports in the literatures by using nitroso sulfide(1,1-dimethylthio-2-nitroethylene)?-1 and various amines ?-2 that easily obtained as the starting materials with ethanol as solvent in refluxing conditions.In the fourth chapter,a simple,efficient,and selective synthetic route for the synthesis of a series of pyrimidines IV-5??-7 by the acylation reaction of heterocyclic ketene amines 1?3 and phenyl isocyanate IV-4 with 1,4-dioxane as solvent at room temperature was described,the yield of the target compounds was 78%-98%.The structures of the above three types of compounds were fully characterized by 1HNMR,13CNMR,IR and HRMS.The single crystals of some of the compounds were characterized by X-Ray crystallography,which further confirmed the structure of the compounds.