Studies On C-N Bond Formation Based On The Cyclohexanone Dehydrogenation Aromatization Reaction

With the rapid progress of sustainable development of society and economy, the chemistry also has a continuous progress, therefore, the area of organic synthesis should have higher, more innovative requirements. The nitrogen-containing organic compound has a broad application prospects in the relevant chemistry field, such as organic synthesis, materials, drugs, and other natural products, Driven by the demands of these compounds, building C-N bonds in organic chemistry has become an important research goal and one of the hotspots. In recent years, there were a lot of literature which introduced the methods of building C-N bonds. With the rise of green chemistry, developing practical new ways that contained readily available raw materials, mild conditions, simple operation for C-N bond formation has very important significance.The traditional coupling reaction of aromatic compounds, usually need two or more aromatic molecules or aromatic heterocyclic molecules as raw materials, through coupling reaction with functionalized substrates to achieve the goal. Cyclohexanone and its derivatives have the advantage of cheap and available, by dehydrogenation aromatization reaction can provide a new way for the construction of aromatic compounds. this paper use cyclohexanone and its derivatives as the object of this study, carried out the study of cyclohexanone dehydrogenation aromatization and conversion reaction. The main contents are as follows:1. Develpoed a study of Palladium-catalyzed reaction of cyclohexanone and sulfonamide to synthesis N-aryl sulfonamide compounds. Cheap, readily available cyclohexanone under the condition of oxygen, coupled with the sulfonamide to get the target product. This method has a mild and green conditions and the functional group tolerance of the substrate is very good, it also can selectively obtain a series of N-aryl sulfonamide compounds and provide a highly effective new approach for the synthesis of compounds containing C-N bonds.2. Launched a synthesis study of 2-arylbenzoxazole and its derivatives from Cyclohexanone and benzamide compounds. Under the condition of absence any transition metal catalyst, potassium iodide, combined with the p-toluenesulfonic acid and dimethylsulfoxide has achieved the cyclohexanone intermolecular cyclization process with benzamide in “one pot”. In this reaction, a non-aromatic cyclohexanone dehydrogenated and as aryl source, oxygen as the oxidant, it also get a higher reaction yield and a good stability for functional group.