Study On The Arylation Of Azlactones Using A Combination Of Diaryliodonium Bromides And Silver Carbonate

This thesis is focused on the development of a reaction system enabling thearylation of azlactones (oxazolones) using diaryliodonium bromides as the arylsource.Firstly, a series of substituted azlactone substrates were prepared from naturalamino acids following reported methods. Then, a range of diaryliodonium salts werealso prepared following two literature methods with appropriate modifications.In the presence of stoichiometric silver carbonate, the reaction conditions of thearylation of azlactones were optimized, and a co-solvent of CCl4and toluene waschosen to give up to93%yield of the desired arylated products. To illustrate theutility of the product, the hydrolysis of the product was performed to provideα-substituted amino acids. Moreover, a preliminary study on the reaction process wasdone capture of the reactive intermediates, which is in support of a radical process.This reaction provides facile access to α-tetrasubstituted amino acid derivatives.All the new products were characterized by1H NMR,13C NMR, IR and HRMS.