Synthesis Of Dialkyl Nitrogen Aromatic-2-ylphosphonates And The Mechanism Research Of Triphenylphosphine-iodine Promoting Oxazole Ring Formation

The paper consists of two parts, the first part is the synthesis of dialkyl nitrogen aromatic-2-ylphosphonates. Dialkyl nitrogen aromatic-2-ylphosphonates and their derivatives have a wide range of applications. Therefore, the development of the synthetic method of dialkyl nitrogen of aromatics-2-phosphonates is great significance. The most general approach is that dialkyl phosphite used as solvent, N-methoxypyridinium salts reacted with sodium dialkyl phosphites to obtain dialkyl nitrogen aromatic-2-ylphosphonates. Unfortunately, unsteadiness of sodium dialkyl phosphites lead to low yield. Moreover, the condition of synthesis is very harsh. Other methods also have different defects, such as need of high temperature and low temperature or metal.In this thesis, trimethyl phosphite and bromotrichloromethane reacted with quinoline isoquinoline nitrogen oxides to generate a high yield of products without solvent at room temperature.The second part is the mechanism research of triphenylphosphine and iodine promoting the reaction of N-acyl amino acid ester ring into oxazole compounds. Oxazole is a kind of very important chemical intermediate, itself has an irreplaceable role in many aspects. Application of oxazole compounds is more extensive, mainly concentrated on drugs, fluorescent whitening, luminous, imaging, and so on. Our laboratory use triphenylphosphine promoting the reaction of N-acyl amino acid ester ring into oxazole compounds, which has the following advantages:(1) have universality of solvent and the substrate,(2) the reagents are cheap, readily available.(3) reaction operation method is simple, purification of product is easy. We designed a series of reactions to explore the mechanism of the reaction, which preliminarlly was verified by isotope labeling experiment.