Study On The Synthesis Of4(3H)-and4(1H)-Ouinazolinolie Derivatives

Quinazolinone derivatives display a wide variety of biological activities such asantitumor, antimalarial and anticonvulsant activities. The application of quinazolinonederivatives is very wide. In this thesis, we selected three routes to synthesize4(3H)-and4(1H)-quinazolinone derivatives because the reported methods associated with certaindrawbacks. The thesis is mainly consists of three parts.The first part is about the synthesis of3-substituted-4(3H)-quinazolinone derivatives.Thirteen3-substituted-4(3H)-quinazolinone derivatives were synthesized by a threecomponents one-pot reaction of anthranilic acid, amines and ortho esters. All reactionscatalyzed by copper o-toluenesulfonate at room temperature without solvent in13%-99%yields. The synthesis and the activity of the catalyst were investigated.The second part is about the synthesis of2-substituted and2,3-disubstituted-2,3-dihydro-4(1H)-quinazolinone derivatives. Nine2-substituted-2,3-dihydro-4(1H)-quinazolinone derivatives and thirteen2,3-disubstituted-2,3-dihydro-4(1H)-quinazolinone derivatives were synthesized by a threecomponents one-pot reaction of isatoic anhydride, aldehydes and ammonium salts or primaryamines using732-strong acidic cation-exchange resin as the catalyst in EtOH/H2O solution(v/v=1/3) under reflux in80%-95%and74%-98%yields, respectively. The activity of thecatalyst and the probable mechanism for the reaction were investigated.The third part is about the synthesis of2-substituted-2,3-dihydro-4(1H)-quinazolinonederivatives without catalyst. Sixteen2-substituted-2,3-dihydro-4(1H)-quinazolinonederivatives were synthesized by a two components reaction of2-anthranilamide andaldehydes or ketones in refluxing water in51%-99%yields. The optimal reaction conditionswere investigated.Many unreported4(3H)-and4(1H)-quinazolinone derivatives have been synthesized inthe experiments. Their structures were confirmed by IR,1H NMR and elementary analysis.