Multi-component One-pot Synthesis Of Imidazopyridine Sulfide And Benzenesulfinic Acid Sulfose Derivatives

C-S bond and S-SO₂ bond are extremely valuable chemical bonds,and their structure can be seen in many sulfur-containing drugs already on the market.Therefore,the development of novel,convenient and efficient synthetic methods to construct new C-S bonds and S-SO₂ bonds is a field of research that many organic and pharmaceutical chemists are keen on.Imidazopyridine is a kind of skeletal structural unit with good biological activity,and has great potential application prospects in the fields of medicine and materials.and a series of aryl sulfide-substituted imidazopyridines were obtained by using tetrahydrofuran as a solution and benzenesulfonyl chloride as a sulfur source without using any metal catalyst.It provides the possibility for future activity research.In addition,we also studied the synthesis of glycosyl phenylthiosulfonates,which has potential biological activity and is also a good S-glycosylation reagent.We use glycosyl bromide as a reactant,without using any catalytic system,through a one-pot three-component reaction strategy to synthesize such compounds.The main work of this thesis includes the following two parts:Part I:we use imidazopyridine compound as the reactant,benzenesulfonyl chloride,hydrazine hydrate as the reaction sulfur source and another reactant,THF as the reaction solvent,through efficient,environmentally friendly multi-component one-pot reaction method to obtain the aryl sulfide-substituted derivative.All of the reactions gave the desired product in good yield.Part II:we use a variety of glycosyl bromide as a glycosyl donor,acetonitrile as a reaction solvent,and sulfur powder and sodium benzenesulfinate in a nitrogen atmosphere,also through efficient,environmentally friendly multi-component one-pot reaction method to obtain a variety of glycosyl phenylthiosulfonates.The compounds obtained by this method provide new possibilities for the subsequent sulfurization of other compounds,and have a good application prospect.In this thesis,two kinds of multi-component one-pot reactions were developed.The reaction conditions were environmentally friendly and mild.The synthesis of imidazopyridine thioether compounds and glycosyl phenylthiosulfonates were completed without metal catalysis.Two types of reactions have good innovation,avoiding the traditional multi-step synthesis,good anti-substrate universality,cheap and easy to obtain raw materials,and easy post-processing.