Study On The Aromatization Of Dihydrogenpyrimidine Derivatives And The Synthesis Of N-aryl Phosphinecarboxamides

In organic synthesis, it is important of a reaction means. to synthesis new organic compounds by oxidative dehydrogenation was developed fastly in recent years. Because the structure of heterocyclic dihydropyrimidine is an important intermediate in the organic heterocyclic chemistry and it also has a variety of biological activities. Therefore, the synthesis of this kind of compounds has received considerable attention in the field of organic heterocyclic chemistry. It is certain development of the oxidative dehydrogenation to build a stable heterocyclic pyrimidine. This method has many advantages, such as many kinds of oxidant and wide range of substrate application.Since Becker and co-workers isolated the 2-phosphaethynolate anion(P?C-O-) in 1992, the synthesis of 2-phosphaethynolate anion and its utilizations in the synthesis of phosphorus-containing organic compounds and heterocycles have been gained much attentions. In particular, nearly three years, it made a series of research results based on the 2-phosphaethynolate anion(P?C-O-) as the starting materials to synthesis of containing phosphorus organic compounds. Thus, it is of great significance to continue exploring this kind of reaction.The main contents of this thesis are as follows: Chapter I: In this thesis, the oxidation processes of dihydropyrimidine from different oxidants were reviewed, On the other side, we simply summarized the preparation and structure characteristics of 2-phosphaethynolate anion and its the organic chemical reactions about 2-phosphaethynolate anion. Chapter II: Cu(OAc)2/1,10-Phen/O2 system catalyzed of oxidation the dihydrogenpyrimidine and dihydrogenpyridine derivatives, giving a series of oxidation products was investigated. The adaptation scope of the substrate was examed, and a large of reaction was explored. The structure of the target product was confirmed by 1H NMR and 13 C NMR analysis. Chapter III: Pd(OAc)2/DPE-phos/2-methyl-1,3-butadiene system catalyzed the oxidative dehydrogenation of the dihydrogenpyrimidine and dihydrogenpyridine derivatives, the a series of oxidation products were obtained. The optimum reaction conditions were explored from the aspects of oxidant, catalyst, ligand, reaction time, solvent and so on. The structure of the target product was confirmed by 1H NMR, 13 C NMR analysis. Chapter IV: Study on the reaction of N-aryl phosphinecarboxamides based on 2-phosphaethynolate anion to synthesize N-aryl phosphinecarboxamides was studied. The structure of the target product was confirmed by 1H NMR, 13 C NMR, and X-ray analysis.