| Summary: | 碩士 === 國立臺灣師範大學 === 化學系 === 100 === C-Aryl-substituted uridine derivatives are an important class of pyrimidine nucleoside analogs that has received considerable attention in recent years. Very few examples of 6-aryluridines have been reported in the literature.
In general, the introduction of an aryl group at 6-position of uracil was limited to the following two ways: (1) photochemical arylation from the 6-iodouridines. (2) Suzuki-Miyaura and Stille cross-coupling reaction from 6-iodouridines. Both methods were restricted by the difficulty for the preparation of 6-iodouridines.
In the past decade, the direct C-H activation for arylation has become an effective method for the introduction of diverse aromatic and heteroaromatic substituents. The focus of this thesis was to develop an effective method which could directly activate the C-H on the uracil or 4-pyridone to undergo the coupling reaction with aryl iodides.
Herein, we reported a general and practical synthesis of 6-aryl-1,3-dimethyluracil derivatives from 1,3-dimethyluracil (1,3-DMU) derivatives via the copper-mediated C-H bond activation as a reaction model for uridine. The reaction scope is generally applicable to a variety of uracil derivatives. In addition, the deuterium isotope studies were carried out in order to gain insight into the reaction details. A preliminary reaction mechanism was proposed based on the isotope effect data.
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