Studies On Lewis Acid Catalyze Quinazoline-N-oxide To Sythesis Quinazoline(Ketone) Derivatives

Quinazoline derivatives and quinazoline ketone derivatives having widely existedin natural and have biological activity, their frameworks play an important role infields of insecticide, disinfection, antivirus, anti-inflammatory, anti-hiv andantineoplastic and agricultural chemicals. Introducting different activity group on thequinazoline framework can get a series of activity quinazoline derivatives, this workwill be very significant. Depend on these, this dissertation mainly centers on1,3-dipolar cycloaddition reaction for the synthesis of quinazoline derivatives andquinazoline ketone derivatives.The paper is divided into four parts.Firstly, we summaried the development of the quinazoline (ketone) derivativesand their activity. We also introducted the1,3-dipolar cycloaddition reaction and itsapplication on organic synthesis.Secondly, the unexpected4-aminoquinazoline derivatives were obtained through1,3-dipolar cycloaddition reaction. The stable nitrone1,3-dipoles were reacted withcarbodiimide via In(OTf)3or SbCl3catalyzed giving rise to aminoquinazolinederivatives which may undergo a procedure of cycloaddition, rearrangement to obtaintwo kinds of4-aminoquinazoline derivatives.Thirdly, the stable nitrone1,3-dipoles were reacted with carbodiimide inmicrowave conditions via FeCl36H2O. The reaction had green reacting condition,short reacting time and also showed good atom economy.Finally, an efficient route of Cu-catalysted to synthesis quinazoline ketonderivatives was presented. We used N,N-substitude foramide and nitrone1,3-dipolesas raw martierial, BPO was oxidant, finally we obtained different quinazoline ketonecarbamate derivatives.