The Synthetic Study Of Tetrahydroquinolines And Spiroisoxazoles Compounds

The structure of tetrahydroquinoline and spiroisoxazole are found in many natural products and play an important role in the metabolism of living organisms.They can be found in many alkaloids.The activity studies showed that they showed good activity in inhibiting virus,fungus and cancer.They are widely used in medicine,agriculture and animal husbandry.Therefore,it is of great significance to carry out research on these two kinds of compounds to find efficient,cheap and green synthetic methods and to promote the practical application of their biological activities.This thesis is divided into two parts:The first part is the study of the tetrahydroquinoline compounds,mainly includes four chapters: the first chapter is research review on the tetrahydroquinoline compounds,which mainly includes the research background and synthetic methods(Aza-Diels-Alder reaction synthetic method,photocatalytic amino acid derivatives decarboxylation method,nitro compounds condensation method catalyzed by cesium carbonate).The second chapter is the preparation of maleimide intermediates: a total of 11 maleimides were synthesized by acetic anhydride method.Eleven unreported tetrahydroquinoline compounds were synthesized by using these derivatives as substrates and by the three components one-pot synthetic method catalyzed by citric acid/kaoline.The third chapter is the synthesis of maleimide intermediates and the four components one-pot synthesis catalyzed by citric acid/kaoline of 10 tetrahydroquinoline compounds,which have been not reported in references.On the basis of the experiments of the second and third chapter,the fourth chapter is aiming at systematic improvement of previous synthetic method of this kind of compounds: using mixed solvent,step by step to join substrates,greatly reducing the dosage of catalyst,and adopting recrystallization for purifying products.The experiment efficiency could be improved by more than five times because of the four improvements.Fourteen new tetrahydroquinoline compounds were synthesized by this method,which have been not reported in references.The second part is the study of spiroisoxazole compounds,includes two chapters.the first chapter is the research overview of spiroisoxazoline compounds(it had been published),mainly including four aspects: the research background of spiroisoxazoline compounds,the synthetic methods of this compounds,biological activity of this compounds,the conclusion and prospect.The second chapter is the study on spiroisoxazolidine compounds with acridine group,which mainly includes three aspects: the research background of acridine compounds and spiroisoxazolidine compounds,the synthesis of intermediates of spiroisoxazolidine compounds with acridine group [9-methyl acridine,methylene cyclohexane and methylene cyclopentane,C-(9-acridinyl)-N-(4-N,N-dimethyl phenyl)nitrone,C-(9-acridinyl)-N-(4-N,N-diethyl phenyl)nitrone,C-(9-acridinyl)-N-(4-hydroxy phenyl)nitrone];The probable reasons for the intermediates failing to generate the target products as our expect were analyzed.