Synthesis And Characterization Of Derivatives Of Triazinone

Triazinone is a kind of heterocyclic compounds with potential biological activity. It has been an important method for the development of new drugs to design molecules, to synthesize lead compounds and to optimize molecular structure. Pymetrazine with insecticide activity represents a typical type of triazinone compounds, and owns the characteristic with high efficiency, low-toxicity and friendly environment, and attracts wide attention for its special action.Pymetrazine is chosed as the lead compound, and 21 compounds were firstly designed and synthesized. These compounds were characterized by introducing phenyl derivatives with different functional groups to replace pyridine ring with the isosteric principle and the method of homogeneous synthesis and reasonable biologically designing in order to find new compounds with potential biological activity. These compounds were confirmed by IR, H NMR and MS spectra.The synthesis of the intermediate amidetriazinone was a crucial step in the synthesis of triazinone. Ethyl acetate was used as the initial material then was carried out for five steps hydrazine hydrate, triphosgene, chloroacetone, hydrazine hydrate respectively with the yield of 59.8%. It was found that the ring-expanding reaction occured easily in the condensation of hydrazinolysis reaction and the side reaction could be restrained by controlling the reaction temperature. In addition, the hydrolytic reaction to prpare amide was very important. We studied the reaction parameters and the optimized conditions was with (7wt%) aqueous chlorine hydride solution for 5h to obtain the yield of 90.6%.The total yield of pymetrazine was up to 52.9% and the purity of the product from HPLC ananlysis was 99.95%. Some kinds of phenyl derivatives with different functional groups including O Cl F, such as OCH3 CF3 OH, were introduced to phenyl different positions and the total yield of theses compounds were 31.3%~55%. We investigated the effect of defferent substitutional phenyl groups and different positions on the spectra properities via the data from IR, ~1H NMR and MS analysis.