Synthesis Of Pyrimidine Functionalized1,4,5-trisubstituted1,2,3-triazole Derivatives And Aryl Thioether/Ether Derivatives

1,2,3-Triazole compounds is a kind of important heterocyclic compounds inmedicinal chemistry, material chemistry, organic chemistry and organometallicchemistry, because of its unique pharmacological activity and chemical properties.Compared with the1,4-and1,5-disubstituted triazole,1,4,5-trisubstituted triazole hasmore diversity, and its regioselectivity synthetic research is becoming a hot spot.In this thesis, the synthetic methods for the1,4,5-trisubstituted1,2,3-triazoleswas summarized. Using Biginelli3,4-dihydropyrimidinone/thione as starting material,we have developed an efficient method for the synthesis of pyrimidine functionalizedtrisubstituted of1,2,3-triazole derivatives and a series of pyrimidines functionalisedaryl ether/ethers derivatives. The main contents are summarized as below:1. New pyrimidine C2-functionalized1,2,3-triazoles were synthesized in goodyields by the three-component reaction of pyrimidin-2-yl sulfonates, sodium azide andactive methylene ketones in the presence of K2CO3at RT. This procedure eliminatesthe need to handle organic azides, as they are generated in situ, making this alreadypowerful process even more user-friendly and safe. The structures of componds wereconformed by IR,1H NMR,13C NMR, and MS. The desired products were furtherconfirmed by the X-ray crystal diffraction.2. Pyrimidine functionalized disulfides were synthesized from Biginelli3,4-dihydropyrimidine-2-thiones via DDQ oxidation in the present of NaH. Then thereaction of the disulfides with the benzene methyl ether, indoles and phenolcompounds leading to a series of pyrimidines functionalized aryl thioether/ethers wasstudied. The methods have the advantages of mild reaction conditions and high yields.The structures of the products were conformed by1H NMR,13C NMR, MS, andHRMS.