Study On Synthesis Of β-carboline Derivatives And AAILSs

The dissertation was contained two chapters.β-carboline derivatives aroused widespread interest because of their wide range of biological activities, especially the antitumor activity. In first chapter the synthesis of β-carboline derivatives was investigated. The activity of some reported β-carboline derivatives and their synthetic methods including Pictet-Spengler reaction and Bischler-Napieralski reaction which were irrelant to the synthesis of β-carboline and it’s derivatives were reviewed in this chapter. Then the synthesis of7-bromine-9-methyl-β-carboline and 7-bromine-9-benzyl-β-carboline were investigated. We have synthesized 7-bromine-9-methyl-β-carboline and7-bromine-9-benzyl-β-carboline via Vilsmeier reaction, methylation or benzylation,Henry reaction with nitromethane, reduction reaction, Pictet-Spengler reaction with glyoxylic acid monohydrate and oxidative dehydrogenation with manganese dioxide using 6-bromoindole as starting material. During the oxidative dehydrogenation reaction step, we attempted some oxidation reagents such as KMnO4, DDQ, S8 but failed. Ultimately, we found that reaction can be performed in refluxing xylene using MnO2 as a oxidation reagent. The yield of Pictet-Spengler reaction in the synthesis of7-bromine-9-benzyl-β-carboline was low and the reaction conditions need to be further optimized. At last the Suzuki coupling reaction of7-bromine-9-methyl(benzyl)-β-carboline with arylboronic acids or alkylboronic acids was studied. To our regretful, the yield of coupling reaction especially for alkylboronic acids was low, new methods need to be developed to get the final product in the future.In second chapter, the synthesis of amino-acid ionic liquid surfactants was investigated. In this chapter the types of amino-acid surfactants and it’s synthetic methods were reviewed. Then the synthesis of amino acid isopropyl ester dodecyl sulfate using amino acids as starting material was investigated. Initially the amino acids(glycine, alanine, valine and proline) was reacted with isopropanol in the presence of thionyl chloride to give the amino-acid isopropyl ester hydrochloride,which was then reacted with sodium dodecyl sulfate in hot water to generate amine acid isoproyl ester dodecyl sulfate. The type of extraction solvent during the synthesis of isopropyl amino acid dodecyl sulfate was studied, the final choice of ethyl acetateas extraction solvent give the target products with satisfactory yield.