The Study For The Synthetic Technics Of A Series Of Tryptamine Derivatives

In the past several decades, the derivatives of tryptamine with the pharmacological and physiological activity , which were used widely in clinic and achieved well-pleasing results,have got the broad regards from the chemistry researchers all over the world. It has been proved that its pharmacological and physiological activity is closely connected with its structures. The subtle changes in the hetercyclic and in the substitution of its 3-position side chain will give rise to the enormous changes in the active aspect of tryptamine derivatives. These facts have been testified by a good number of experiments. Meanwhile, the scientists gave the reasonable explanations for the structure-activity of the substances.The synthetic methods for the tryptamine derivatives of Indole are diverse. The adopted method with which the requisite production is obtained is via a series of preparation processes which are by and large the synthesis of the substituted Indole cycle, the introduction of the 3-position side chain in the cycle and the further changes for the substitutions of Indole cycle, etc. On the condition of the substituted Indole as the raw material, because of their less preparation steps and the convenient sources of the raw materials, we select scheme 5,6 to synthesis the production and improve the routes from the numerous schemes which have been set out. Two schemes which are cooperating with each other in use will be able to prepare in effect the tryptamine derivatives of the primary-amine type and the non-primary-amine type. For the non-primary-amine derivatives, we adopt the oxalyl chloride , the substituted amine to introduce the 3-position side chains by scheme 6, then to reduce the side chains introduced just now with lithium aluminum hydride(LAH), in this way ,we can get the tryptamine production as this type .In the course of reaction ,we must protect the reactive function groups such as the hydroxy group in effect so that the reaction in all steps can carry on favorably. We select the acetoxy group to protect the hydroxy group from a great number of the protection methods for the hydroxy group. For theprimary-amine derivatives, we introduce the side chains by concentrating the substituted Indole-3-aldehyde and the nitro compound in the presence of catalyst anhydrous ammonium acetate with scheme 6. by the same token , by reducing the side chains with LAH ,we also can get the tryptamine production as this type . Moreover , we take advantage of the Vilesmier method to synthesis the substituted Indole-3-aldehyde as the raw material in using scheme 5 to prepare the primary-amine derivatives. In addition, after introducing the 3-position side chain, we are capable of changing the side chain into the tryptamine production that we need with scheme 5,6. In the process of preparation, to simplify the preparation steps of the tryptamine such as methyl isopropyltryptamine(MIPT), we synthesis expediently methyl isopropylamine(MIPA) as the requisite raw material by using the cheap raw material.We synthesis and study mainly in the improvement posture 4-hydroxttryptamine derivatives and 5-methoxytryptamine derivatives as the goal molecules in the dissertation. It focuses on preparing these derivatives in batches in the course of synthesis, following the guidance principle of decreasing the production cost, increasing the production ratio and operating expediently the reaction. The advantages are able to be testified by the predominant operation methods and demonstrated by the satisfying experiment results (datum) from the experiment under way. In the experiment section, I also give descriptions to the mechanism for those reactions in details and spare no effort to provide the reasonable explanations for them.