The Synthesis Of Indole Alkaloids Containing Guanidine And2-imine Tetrahydroimidazo

Indole alkaloids is the largest number of alkaloids, accounting for about a quarterof the alkaloid total number. Most of indole alkaloids have significant biologicalactivity, a lot of these drugs, such as vinblastine, reserpine, strychnine, Ergometrine,etc., have been used in clinical treatment. Guanidine compound also has a goodbiological activity, the guanidino-containing drugs have been widely used inhyperglycemia, hypertension and viral infections treatment. Even though there aremany different kinds of indole alkaloids, the synthesis of guanidine containing indolealkaloids are rarely reported. So proposed one such compound synthesis method hasimportant significance.This thesis is divided into three parts. The first part includes the classification,applications, and synthesis of indole alkaloids, and application and synthesis of theguanidino compounds. This section first describes the classification of the indolealkaloids and its role in the nervous system, cardiovascular system, can affect uterineactivity, anti-tumor, anti-viral,etc. in biological activity. And then focuses on thesynthesis of indole alkaloids. Finally, we introduce the application of guanidines, andsummarize the method of synthesis of guanidino compound. It is provide a referenceon the novl guanidino containing indole alkaloids synthetic route design andsynthesis.The second part is the main part of the paper. On the basis of the results ofprevious research in the laboratory and reference to other methods of synthesis ofindole alkaloids, we designed and synthesized a series of novel guanidine containingindole alkaloid derivatives. Tryptophan as a starting material, by the esterificationreaction and Mannich reaction we build a six-membered aza heterocyclic. And itreacted with carbodiimide intermediates that is obtained Pbf activated thiourea bydesulphurization reaction. Then via intramolecular ester amine solution we build aguanidino containing Five-membered aza heterocyclic. In the building of theguanidino-containing five-membered aza heterocyclic, We apply the one-pot tandemreaction on the reaction of the synthesis guanidino and intramolecular ammonolysis reaction of ester. It simplified the reaction process and improved the reaction yield.During the synthesis, we use two synthetic methods to synthesize importantintermediates Pbf-NCS,and contrast the advantages and disadvantages of the twomethods. Finally, we studied the influence of steric hindrance to the reaction. Thesynthetic route has lots of advantage such as simple, efficient, and operability, etc. Itprovided an effective synthetic method for the guanidine containing the indolealkaloid synthesis.The third part is mainly to design and try to synthesis the2-iminetetrahydroimidazo. Aziridine chalcone reacts with the intermediate of carbodiimidewhich is obtained from the Pbf activated thiourea to give the2-iminetetrahydroimidazo。...